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The Polonovski Reaction

  1. David Grierson

Published Online: 15 OCT 2004

DOI: 10.1002/0471264180.or039.02

Organic Reactions

Organic Reactions

How to Cite

Grierson, D. 2004. The Polonovski Reaction. Organic Reactions. 39:2:85–295.

Author Information

  1. Gif sur Yvette, National Center of Scientific Research, Cedex, France

Publication History

  1. Published Online: 15 OCT 2004

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Abstract

In connection with their interest in the isolation and medicinal properties of the “gen alkaloids” (N-oxides), Max and Michel Polonovski reported in 1927 their discovery that the treatment of a tertiary amine N-oxide with acetic anhydride or acetyl chloride results in a rearrangement in which one of the alkyl groups attached to nitrogen is cleaved, and the N-acetyl derivative of the corresponding secondary amine and aldehyde are obtained.

As the original work by the Polonovskis was mainly carried out on bicyclic tropane N-oxide derivatives, the products of the reaction were the demethylated amides and formaldehyde. The reaction was thus looked upon as a means of effecting N-demethylation of tertiary amines. As such it was, and still remains, a viable alternative to the use of cyanogen bromide, alkyl chloroformates, azocarboxylic esters, or nitrous acid for this purpose. These methods often require more drastic conditions and/or promote unwanted side reactions.

The central feature of the Polonovski reaction is the transformation of an N-oxide to an iminium ion intermediate. Depending on the structure of the substrate and the acid anhydride or other activating reagent employed, iminium ion formation can occur through loss of an α hydrogen, or through fragmentation of a Cα[BOND]carbon bond. Again, depending on conditions, the reaction will either stop at this stage and iminium ions become the Polonovski products, or proceed to give enamines or tertiary amides and/or secondary amines and aldehydes. The often close relationship between structure and reaction conditions, which determine both product types and reaction regiochemistry, is discussed.

In its initial stages the Polonovski reaction resembles other reactions in which a tertiary amine is oxidized through interaction of the pair of electrons on nitrogen with an agent X followed by elimination of the elements of HX. Reagents like lead tetraacetate, N-bromosuccinimide and in particular mercuric acetate have been employed for this purpose. However, the Polonovski reaction can offer certain advantages in selectivity and experimental ease.

In principle, any reagent capable of activating the N-oxide oxygen could promote the Polonovski reaction. However, three major types of activating agents, acid anhydrides and chlorides (including chloroformate esters), iron salts and complexes, and sulfur dioxide, are usually employed.

Perhaps the most important contribution to the use of the Polonovski reaction in modern organic synthesis was the discovery in the 1960s that on replacing acetic anhydride by trifluoroacetic anhydride the reaction could be stopped at the iminium ion stage. Considering the rich chemistry of iminium ions, many applications of this modified, or Polonovski–Potier, reaction have appeared in the literature, the most spectacular of which was the first successful approach to the synthesis of the indole antitumor agents of the vinblastine group.

In this chapter the discussion is limited to examples of the Polonovski reaction in which the abovementioned activating reagents are employed. The coverage is restricted to tertiary amine oxides in which at least one of the substituents on nitrogen is an alkyl group. Both acyclic and cyclic amine oxides such as piperidine N-oxide fall into this category, whereas heteroaromatic N-oxides do not. With the exception of one special case, nitrones are also omitted from the discussion.

The literature coverage includes articles appearing before the end of August 1988.

Keywords:

  • Polonovski reaction;
  • scope;
  • limitations;
  • acylating agents;
  • iron-based reagents;
  • sulfur dioxide;
  • carbon-hydrogen eliminations;
  • synthetic applications;
  • C[BOND]C fragmentations;
  • iron salts;
  • silicon;
  • selenium;
  • experimental procedures;
  • indole alkaloids

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Compound Information
Molecular Weight:0
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:119.378
Molecular Formula:CHCl3
InChIKey:HEDRZPFGACZZDS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:151.2056
Molecular Formula:C9H13NO
InChIKey:ASPNHHABGUHHOD-BDAKNGLRSA-N
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Compound Information
Molecular Weight:129.2001
Molecular Formula:C7H15NO
InChIKey:WGVVTBRJBGRJBI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:199.333
Molecular Formula:C12H25NO
InChIKey:MWHUEUWCLCIUFP-PHIMTYICSA-N
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Compound Information
Molecular Weight:141.2108
Molecular Formula:C8H15NO
InChIKey:LLBGYKKMEQGHCA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:196.2462
Molecular Formula:C10H16N2O2
InChIKey:SFEGIRUEAZTXED-UHFFFAOYSA-N
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Compound Information
Molecular Weight:157.2102
Molecular Formula:C8H15NO2
InChIKey:AGFHIYSVIRKUQX-YDOKIASTSA-N
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Compound Information
Molecular Weight:155.625
Molecular Formula:C8H10ClN
InChIKey:IONGEXNDPXANJD-UHFFFAOYSA-N
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Molecular Weight:143.2267
Molecular Formula:C8H17NO
InChIKey:MMAXOAIHEPNELR-UHFFFAOYSA-N
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Molecular Weight:171.2798
Molecular Formula:C10H21NO
InChIKey:MMKQDILVYWBXOH-UHFFFAOYSA-N
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Molecular Weight:127.1842
Molecular Formula:C7H13NO
InChIKey:FDJKLIVKKYFLSA-UHFFFAOYSA-N
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Molecular Weight:225.2512
Molecular Formula:C10H18F3NO
InChIKey:BLBHGEFSNRUWLF-UHFFFAOYSA-N
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Molecular Weight:155.2374
Molecular Formula:C9H17NO
InChIKey:NVEYVSRXOFPIRE-UHFFFAOYSA-N
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Molecular Weight:171.2368
Molecular Formula:C9H17NO2
InChIKey:OBUPEAULLRNENN-UHFFFAOYSA-N
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Molecular Weight:223.3544
Molecular Formula:C14H25NO
InChIKey:KLVOTXOWYVNGSJ-UHFFFAOYSA-N
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Molecular Weight:149.1897
Molecular Formula:C9H11NO
InChIKey:LMTGCJANOQOGPI-UHFFFAOYSA-N
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Molecular Weight:152.2367
Molecular Formula:C9H16N2
InChIKey:HBGNDACDNFEHRJ-UHFFFAOYSA-N
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Molecular Weight:211.3437
Molecular Formula:C13H25NO
InChIKey:HSTWRLXGGNIZAS-TXEJJXNPSA-N
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Compound Information
Molecular Weight:150.2209
Molecular Formula:C9H14N2
InChIKey:MIQUNXLIWZVSSY-UHFFFAOYSA-N
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Molecular Weight:138.2102
Molecular Formula:C8H14N2
InChIKey:PRPJCKZJCBWSDT-UHFFFAOYSA-N
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Molecular Weight:171.624
Molecular Formula:C8H10ClNO
InChIKey:OINLEBHBTKRSTR-UHFFFAOYSA-N
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Molecular Weight:113.1576
Molecular Formula:C6H11NO
InChIKey:UHMWMTXBOBUXRV-UHFFFAOYSA-N
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Molecular Weight:208.2569
Molecular Formula:C11H16N2O2
InChIKey:YQFWNTHVKBBPNP-UHFFFAOYSA-N
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Molecular Weight:222.2835
Molecular Formula:C12H18N2O2
InChIKey:RIQJZTRFVVOGPJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:151.2056
Molecular Formula:C9H13NO
InChIKey:MOYHVSKDHLMMPS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:198.2637
Molecular Formula:C13H14N2
InChIKey:NYHVHPFJERLZRH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:164.2474
Molecular Formula:C10H16N2
InChIKey:CNSYHKJGHWADCR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:185.2634
Molecular Formula:C10H19NO2
InChIKey:YLOYTNANHIYSDX-UHFFFAOYSA-N
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Molecular Weight:Not Available
Molecular Formula:Not Available
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Molecular Weight:175.227
Molecular Formula:C11H13NO
InChIKey:BXRRISZKFONWJO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:114.1855
Molecular Formula:C7H14O
InChIKey:Not Available
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Molecular Weight:189.2536
Molecular Formula:C12H15NO
InChIKey:RMBANEPTDAKKLG-UHFFFAOYSA-N
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Molecular Weight:152.214
Molecular Formula:C8H8OS
InChIKey:WBISVCLTLBMTDS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:269.747
Molecular Formula:C12H12ClNO2S
InChIKey:Not Available
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Molecular Weight:101.19
Molecular Formula:C6H15N
InChIKey:ZMANZCXQSJIPKH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:167.205
Molecular Formula:C9H13NO2
InChIKey:ZWHDTCLYKBKEOX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:268.3089
Molecular Formula:C13H20N2O4
InChIKey:LWUITGIUEVYTCH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:163.2163
Molecular Formula:C10H13NO
InChIKey:ZMYCGFKAPZHNPC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:62.0248
Molecular Formula:CH2O3
InChIKey:Not Available
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Molecular Weight:243.4179
Molecular Formula:C12H25NO2Si
InChIKey:DQTJFFPUNOUBOE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:196.2032
Molecular Formula:C9H12N2O3
InChIKey:IBEQWAMLXQKOLD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:163.2163
Molecular Formula:C10H13NO
InChIKey:QCIITDBFPWKIRR-UHFFFAOYSA-N
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Molecular Weight:155.1943
Molecular Formula:C8H13NO2
InChIKey:BWDLDXCAAQLGCV-SRSLHRDFSA-N
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Compound Information
Molecular Weight:123.1955
Molecular Formula:C8H13N
InChIKey:IIYSNNBEZBAQCQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:268.3089
Molecular Formula:C13H20N2O4
InChIKey:KUVHHNPXPQTCRJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:117.1894
Molecular Formula:C6H15NO
InChIKey:LFMTUFVYMCDPGY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:185.2634
Molecular Formula:C10H19NO2
InChIKey:KWEMNZJZFGSVRN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:73.0938
Molecular Formula:C3H7NO
InChIKey:ZMXDDKWLCZADIW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.2209
Molecular Formula:C9H14N2
InChIKey:FCHQFFSFJVQEER-UHFFFAOYSA-N
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Compound Information
Molecular Weight:143.2267
Molecular Formula:C8H17NO
InChIKey:JZXKPSBHOOVNPL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:140.567
Molecular Formula:C7H5ClO
InChIKey:PASDCCFISLVPSO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:145.201
Molecular Formula:C10H11N
InChIKey:XETNILDBKBCRLR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:84.1164
Molecular Formula:C5H8O
InChIKey:BGTOWKSIORTVQH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:179.2157
Molecular Formula:C10H13NO2
InChIKey:ZWDMLQALYVVXTM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:155.625
Molecular Formula:C8H10ClN
InChIKey:QDCPXCIPVQJVDD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:84.0066
Molecular Formula:CHNaO3
InChIKey:UIIMBOGNXHQVGW-UHFFFAOYSA-M
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Compound Information
Molecular Weight:197.661
Molecular Formula:C10H12ClNO
InChIKey:RGPBSGXDZOWWRE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:151.2056
Molecular Formula:C9H13NO
InChIKey:ZTKDMNHEQMILPE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:87.1204
Molecular Formula:C4H9NO
InChIKey:FXHOOIRPVKKKFG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:165.2322
Molecular Formula:C10H15NO
InChIKey:YOIQWFZSLGRZJX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:173.2542
Molecular Formula:C12H15N
InChIKey:BJEJAHKSZFFDOZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:111.1418
Molecular Formula:C6H9NO
InChIKey:FYVXQMLPGIHTKN-UHFFFAOYSA-N
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Molecular Weight:155.2374
Molecular Formula:C9H17NO
InChIKey:CWAQLBZCYZCXGU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:167.205
Molecular Formula:C9H13NO2
InChIKey:HVTABFZNOWGFGP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:127.1842
Molecular Formula:C7H13NO
InChIKey:SBLOBEZQKRXGTD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:165.2322
Molecular Formula:C10H15NO
InChIKey:VFEDZSVUSDDGOC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:208.2569
Molecular Formula:C11H16N2O2
InChIKey:RIJVNIDTRVYFTD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:121.1796
Molecular Formula:C8H11N
InChIKey:Not Available
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Molecular Weight:163.2163
Molecular Formula:C10H13NO
InChIKey:NQXVNLHPEJBZAT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:30.026
Molecular Formula:CH2O
InChIKey:Not Available
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Molecular Weight:179.2157
Molecular Formula:C10H13NO2
InChIKey:BZSWWJLVPTULPS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:103.1628
Molecular Formula:C5H13NO
InChIKey:HBXJMYFBDFGRPI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:231.2143
Molecular Formula:C11H12F3NO
InChIKey:ISRUPAMWGCUHNK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.2367
Molecular Formula:C9H16N2
InChIKey:GFXBEAICVBZRGP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:171.2383
Molecular Formula:C12H13N
InChIKey:KKCMGDGJMRZKJP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:199.2469
Molecular Formula:C10H17NO3
InChIKey:YLPLGLUMXZBKDM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:181.2316
Molecular Formula:C10H15NO2
InChIKey:KLLXXDVDSJFDFM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:171.2368
Molecular Formula:C9H17NO2
InChIKey:XVKIWLKINNPHOU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:60.052
Molecular Formula:C2H4O2
InChIKey:QTBSBXVTEAMEQO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:219.2036
Molecular Formula:C10H12F3NO
InChIKey:DKXQQCNSIQYFKT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:185.2203
Molecular Formula:C9H15NO3
InChIKey:JRSNAEUXJQQGIT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:181.2316
Molecular Formula:C10H15NO2
InChIKey:AOGVHKMEGRCAHC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:18.0153
Molecular Formula:H2O
InChIKey:XLYOFNOQVPJJNP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:196.2462
Molecular Formula:C10H16N2O2
InChIKey:LKTNLARLJDYMCI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:183.635
Molecular Formula:C9H10ClNO
InChIKey:SHWDMQXUSIUGJW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:163.2163
Molecular Formula:C10H13NO
InChIKey:FSSVIYSWRLKICW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:26.0174
Molecular Formula:CHN
InChIKey:XFXPMWWXUTWYJX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:58.1023
Molecular Formula:C3H8N
InChIKey:HYHSFFFCLDOXCJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:34.0147
Molecular Formula:H2O2
InChIKey:MHAJPDPJQMAIIY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:163.2163
Molecular Formula:C10H13NO
InChIKey:QKIDBCKIVIQWLL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.1943
Molecular Formula:C8H12N2
InChIKey:BMQKWWKZACXDAP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:165.2322
Molecular Formula:C10H15NO
InChIKey:VHLGRKTXILMMPF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:167.205
Molecular Formula:C9H13NO2
InChIKey:RKTPOXAAOHCGDQ-OCAPTIKFSA-N
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Compound Information
Molecular Weight:159.2691
Molecular Formula:C9H21NO
InChIKey:SOVWKKYLBJMOPM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:139.1949
Molecular Formula:C8H13NO
InChIKey:WSVVZKJLNLRRKM-VGMNWLOBSA-N
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Compound Information
Molecular Weight:133.1888
Molecular Formula:C6H15NO2
InChIKey:MRYQZMHVZZSQRT-UHFFFAOYSA-M
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Compound Information
Molecular Weight:106.1219
Molecular Formula:C7H6O
InChIKey:HUMNYLRZRPPJDN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:102.0886
Molecular Formula:C4H6O3
InChIKey:Not Available
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Compound Information
Molecular Weight:74.1216
Molecular Formula:C4H10O
InChIKey:RTZKZFJDLAIYFH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:199.2469
Molecular Formula:C10H17NO3
InChIKey:ZFBMNSGMXGBSLU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:225.2842
Molecular Formula:C12H19NO3
InChIKey:MSSWXWJJBJKOEU-GDNZZTSVSA-N
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Compound Information
Molecular Weight:141.2108
Molecular Formula:C8H15NO
InChIKey:NDGBBPPNTWHVLT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:194.2304
Molecular Formula:C10H14N2O2
InChIKey:QQZKUPYZQKMLII-UHFFFAOYSA-N
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Compound Information
Molecular Weight:190.2417
Molecular Formula:C11H14N2O
InChIKey:SSABMTSCLQGWBB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:210.2728
Molecular Formula:C11H18N2O2
InChIKey:BMBYSRPLZCTMIU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:151.2056
Molecular Formula:C9H13NO
InChIKey:QVXHURRSEYIZKN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:197.2741
Molecular Formula:C11H19NO2
InChIKey:HYZCZKAVDFMOJR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:208.2139
Molecular Formula:C10H12N2O3
InChIKey:ICIRAKBVOJIUFC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:191.2695
Molecular Formula:C12H17NO
InChIKey:JXGVBIBIKLZHJU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:141.2108
Molecular Formula:C8H15NO
InChIKey:BSFQRAMYQQRXCW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:155.2374
Molecular Formula:C9H17NO
InChIKey:USMNXTDMOPUHAJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:189.2536
Molecular Formula:C12H15NO
InChIKey:YGANNHALORHAJH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:232.2977
Molecular Formula:C14H18NO2
InChIKey:OWLPGDMSQDSIJJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:115.1735
Molecular Formula:C6H13NO
InChIKey:IDTCRCSCQGCWIY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:177.286
Molecular Formula:C12H19N
InChIKey:IUOVLMNCKHQXQM-NWDGAFQWSA-N
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Compound Information
Molecular Weight:167.205
Molecular Formula:C9H13NO2
InChIKey:WALUWQHOXQHKDI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:157.2117
Molecular Formula:C11H11N
InChIKey:FNEQHKCQXDKYEO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:193.1663
Molecular Formula:C8H10F3NO
InChIKey:HUQOQQKDVJKNGL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:100.1158
Molecular Formula:C5H8O2
InChIKey:YRKCREAYFQTBPV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:78.498
Molecular Formula:C2H3ClO
InChIKey:WETWJCDKMRHUPV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:193.2423
Molecular Formula:C11H15NO2
InChIKey:NQQOVDFKLVAGEB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:141.0917
Molecular Formula:C4H6F3NO
InChIKey:WXBWKMLIVXELSF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:141.2108
Molecular Formula:C8H15NO
InChIKey:XUBIVAHAAJCIGQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:154.2493
Molecular Formula:C10H18O
InChIKey:YKFKEYKJGVSEIX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:122.1677
Molecular Formula:C7H10N2
InChIKey:XPGCXCNNIYNUMX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:137.179
Molecular Formula:C8H11NO
InChIKey:LKQUDAOAMBKKQW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:143.2267
Molecular Formula:C8H17NO
InChIKey:BCEJHALOZVUYAK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:593.757
Molecular Formula:C31H35N3O5S2
InChIKey:UTOGNUXPVHDKAH-JKHIJQBDSA-N
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Compound Information
Molecular Weight:151.1195
Molecular Formula:C7H5NO3
InChIKey:BXRFQSNOROATLV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:210.2728
Molecular Formula:C11H18N2O2
InChIKey:QSOSNCVIJBPBNA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:129.2001
Molecular Formula:C7H15NO
InChIKey:LYJNZDODFLCNJE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:115.1735
Molecular Formula:C6H13NO
InChIKey:AJFDBNQQDYLMJN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:183.635
Molecular Formula:C9H10ClNO
InChIKey:LODSEQRXZMEKSP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:181.2316
Molecular Formula:C10H15NO2
InChIKey:LQVTXXUZTMGSJW-DTORHVGOSA-N
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Compound Information
Molecular Weight:185.651
Molecular Formula:C9H12ClNO
InChIKey:KEATYRIENVHIGB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:179.2588
Molecular Formula:C11H17NO
InChIKey:FDUJGBCHQGYMJK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:171.624
Molecular Formula:C8H10ClNO
InChIKey:MTKKEQBXJZFVLY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:211.2576
Molecular Formula:C11H17NO3
InChIKey:VUSBFPSFXFXJTJ-ZACCUICWSA-N
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Compound Information
Molecular Weight:129.157
Molecular Formula:C6H11NO2
InChIKey:QKGPEEBIQDMBGA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:72.1057
Molecular Formula:C4H8O
InChIKey:WYURNTSHIVDZCO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:196.2462
Molecular Formula:C10H16N2O2
InChIKey:FKHUWPYOGLPVRM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:111.1211
Molecular Formula:C5H10AlN
InChIKey:KWMUAEYVIFJZEB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:177.2429
Molecular Formula:C11H15NO
InChIKey:XKXZFFXZDPWQSF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:210.0314
Molecular Formula:C4F6O3
InChIKey:QAEDZJGFFMLHHQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:50.488
Molecular Formula:CH3Cl
InChIKey:NEHMKBQYUWJMIP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:115.1735
Molecular Formula:C6H13NO
InChIKey:VTGXVUQXDHXADV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.2367
Molecular Formula:C9H16N2
InChIKey:ZNDKGZTXFLTQKE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:762.076
Molecular Formula:C43H59N3O5S2
InChIKey:AGUOEOYJDIKORC-YPALIABXSA-N
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Compound Information
Molecular Weight:75.1097
Molecular Formula:C3H9NO
InChIKey:Not Available
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Compound Information
Molecular Weight:140.567
Molecular Formula:C7H5ClO
InChIKey:AVPYQKSLYISFPO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:191.2695
Molecular Formula:C12H17NO
InChIKey:QHPXQZPBFXJLRI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:149.1897
Molecular Formula:C9H11NO
InChIKey:IMNDHOCGZLYMRO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:151.2056
Molecular Formula:C9H13NO
InChIKey:UJZXIGKNPLTUOZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:164.2474
Molecular Formula:C10H16N2
InChIKey:NKRUCUYMSKUYCJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:46.0684
Molecular Formula:C2H6O
InChIKey:LFQSCWFLJHTTHZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:173.2096
Molecular Formula:C8H15NO3
InChIKey:HPKNETUMJKAJCC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:84.933
Molecular Formula:CH2Cl2
InChIKey:YMWUJEATGCHHMB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:171.2373
Molecular Formula:C9H18NO2
InChIKey:RZTHTCBIQGGUKK-BRPSZJMVSA-N
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Compound Information
Molecular Weight:180.2468
Molecular Formula:C10H16N2O
InChIKey:YXTAMRZTBLUMAL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:135.2062
Molecular Formula:C9H13N
InChIKey:Not Available
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Compound Information
Molecular Weight:179.2157
Molecular Formula:C10H13NO2
InChIKey:MTNYWHUCTUHQIQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:195.3012
Molecular Formula:C12H21NO
InChIKey:XAIHLKSUUURVEW-WPLWPFLGSA-N
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Compound Information
Molecular Weight:178.231
Molecular Formula:C10H14N2O
InChIKey:RWFBQHICRCUQJJ-NUHJPDEHSA-N
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Compound Information
Molecular Weight:127.1842
Molecular Formula:C7H13NO
InChIKey:APTXQWUCXWZLNE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:353.907
Molecular Formula:C18H24ClNO2S
InChIKey:PIZHBGYIKYGXBV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:201.2628
Molecular Formula:C10H19NO3
InChIKey:VFWDSCILESPCAZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:169.2214
Molecular Formula:C9H16NO2
InChIKey:YSCQWKDTYOAYNF-OCAPTIKFSA-N
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Compound Information
Molecular Weight:167.205
Molecular Formula:C9H13NO2
InChIKey:JCQQTWOGPYCHAX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:181.2316
Molecular Formula:C10H15NO2
InChIKey:CBKCZQXUBOSAKU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:210.2728
Molecular Formula:C11H18N2O2
InChIKey:BEDQSDQTTVULID-UHFFFAOYSA-N
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Compound Information
Molecular Weight:117.1463
Molecular Formula:C5H11NO2
InChIKey:DQLJRWJDWPEJRE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:210.2728
Molecular Formula:C11H18N2O2
InChIKey:JEXVMMMDFSKNMS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:259.2988
Molecular Formula:C12H21NO5
InChIKey:ZYDSLSVCVKZDHI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:79.0999
Molecular Formula:C5H5N
InChIKey:Not Available
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Compound Information
Molecular Weight:177.2462
Molecular Formula:C10H15N3
InChIKey:WXKVIDCAOZXYGF-RCAUJQPQSA-N
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Compound Information
Molecular Weight:124.1836
Molecular Formula:C7H12N2
InChIKey:PMTWHXIFGUMFRG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:137.179
Molecular Formula:C8H11NO
InChIKey:Not Available
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Compound Information
Molecular Weight:182.2197
Molecular Formula:C9H14N2O2
InChIKey:BCXKOTWVQPFNJM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.2367
Molecular Formula:C9H16N2
InChIKey:YLUZQIUNDDCKCQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:115.1735
Molecular Formula:C6H13NO
InChIKey:SJCBWLJRMCOJEC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:265.3151
Molecular Formula:C13H22F3NO
InChIKey:HOPPNJYSSMQHLB-AOOOYVTPSA-N
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Compound Information
Molecular Weight:187.2362
Molecular Formula:C9H17NO3
InChIKey:AQWZCYXFPQLYBF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:135.2062
Molecular Formula:C9H13N
InChIKey:JDEJGVSZUIJWBM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:199.634
Molecular Formula:C9H10ClNO2
InChIKey:AECGXMNKQBSSOE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:151.2056
Molecular Formula:C9H13NO
InChIKey:NALMPLUMOWIVJC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:157.2102
Molecular Formula:C8H15NO2
InChIKey:AGFHIYSVIRKUQX-OJOKCITNSA-N
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Compound Information
Molecular Weight:157.2102
Molecular Formula:C8H15NO2
InChIKey:AGFHIYSVIRKUQX-WTPCLMDXSA-N
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Compound Information
Molecular Weight:157.2102
Molecular Formula:C8H15NO2
InChIKey:AGFHIYSVIRKUQX-WKALFLHCSA-N
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Compound Information
Molecular Weight:593.757
Molecular Formula:C31H35N3O5S2
InChIKey:UTOGNUXPVHDKAH-NUNAXRQHSA-N
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Compound Information
Molecular Weight:762.076
Molecular Formula:C43H59N3O5S2
InChIKey:AGUOEOYJDIKORC-SGIQEJNWSA-N
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Compound Information
Molecular Weight:199.333
Molecular Formula:C12H25NO
InChIKey:MWHUEUWCLCIUFP-XYPYZODXSA-N
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Compound Information
Molecular Weight:211.3437
Molecular Formula:C13H25NO
InChIKey:HSTWRLXGGNIZAS-HAQNSBGRSA-N
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Compound Information
Molecular Weight:351.4421
Molecular Formula:C21H25N3O2
InChIKey:ZKZDZFNZMBNWAE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:289.3694
Molecular Formula:C17H23NO3
InChIKey:ZNQZZYYYQYKBLX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:282.3801
Molecular Formula:C18H22N2O
InChIKey:MCEMXDSSQGCWRL-WSPQDMPNSA-N
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Compound Information
Molecular Weight:263.3321
Molecular Formula:C15H21NO3
InChIKey:YYHWYXQYNPKPQL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:195.084
Molecular Formula:Pt
InChIKey:BASFCYQUMIYNBI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:300.4384
Molecular Formula:C19H28N2O
InChIKey:XGXIZNCJSNNUMW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:377.4794
Molecular Formula:C23H27N3O2
InChIKey:VADAOTRHEQABSD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:226.3168
Molecular Formula:C15H18N2
InChIKey:JBRHLGAXJXVJOQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:282.139
Molecular Formula:C2F6O5S2
InChIKey:WJKHJLXJJJATHN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:266.3807
Molecular Formula:C18H22N2
InChIKey:QOCMEFKTIYHEBI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:296.4067
Molecular Formula:C19H24N2O
InChIKey:RBKWHYGWQQBRTM-FOTGFLGGSA-N
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Compound Information
Molecular Weight:380.437
Molecular Formula:C22H24N2O4
InChIKey:DBPXQDNGUYSBPA-IYERYRBDSA-N
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Compound Information
Molecular Weight:368.4263
Molecular Formula:C21H24N2O4
InChIKey:SCBWVOFEDKLZRF-BMKSKLCGSA-N
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Compound Information
Molecular Weight:327.4174
Molecular Formula:C20H25NO3
InChIKey:CQLWHPMAMUBLNG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:363.4528
Molecular Formula:C22H25N3O2
InChIKey:RBPDTKONLCEEII-CHUSEJEBSA-N
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Compound Information
Molecular Weight:314.3789
Molecular Formula:C18H22N2O3
InChIKey:PXGRKUWCZAJKKL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:270.3694
Molecular Formula:C17H22N2O
InChIKey:UMVMHXUWQDUWEV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:382.4528
Molecular Formula:C22H26N2O4
InChIKey:UIVAKGXUTLURSI-QIOXMYBNSA-N
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Compound Information
Molecular Weight:282.3801
Molecular Formula:C18H22N2O
InChIKey:HSGPFKBBMRMFOK-LVPSWPKJSA-N
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Compound Information
Molecular Weight:324.4168
Molecular Formula:C20H24N2O2
InChIKey:FNXYSQNRXOSXLX-LUNMMQQFSA-N
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Compound Information
Molecular Weight:298.4225
Molecular Formula:C19H26N2O
InChIKey:BBLQGKXGUSVYQF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:231.3333
Molecular Formula:C15H21NO
InChIKey:GYRLMNCDIBBHMU-FLPGBKCWSA-N
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Compound Information
Molecular Weight:448.554
Molecular Formula:C27H32N2O4
InChIKey:SPEPUTOAGXBCDS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:287.3535
Molecular Formula:C17H21NO3
InChIKey:MSIMRMSUISRCBB-JQGPAHRUSA-N
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Compound Information
Molecular Weight:267.3224
Molecular Formula:C17H17NO2
InChIKey:AKTHDOOJEVMXEP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:282.3801
Molecular Formula:C18H22N2O
InChIKey:ZGUHKNVOBNLPEI-SILLCRNTSA-N
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Compound Information
Molecular Weight:419.539
Molecular Formula:C24H25N3O2S
InChIKey:YHYXFNHGJVORJF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:370.4421
Molecular Formula:C21H26N2O4
InChIKey:BFVLDYJQFGVNQS-JEIZFFLYSA-N
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Compound Information
Molecular Weight:199.2484
Molecular Formula:C13H13NO
InChIKey:FVXHMONFDNQNAA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:352.4269
Molecular Formula:C21H24N2O3
InChIKey:BFGJGYVLTYYXEO-QTQMJOQSSA-N
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Compound Information
Molecular Weight:247.3327
Molecular Formula:C15H21NO2
InChIKey:RDBHYXGOCNFBOX-VVCCJLAWSA-N
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Compound Information
Molecular Weight:350.411
Molecular Formula:C21H22N2O3
InChIKey:QMWSDSZPXGRFNN-DWIQEWEKSA-N
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Compound Information
Molecular Weight:335.271
Molecular Formula:C18H20Cl2N2
InChIKey:WVTITUVRXHGWBS-AXAGEFLBSA-N
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Compound Information
Molecular Weight:252.3541
Molecular Formula:C17H20N2
InChIKey:YJTDUNDYSBBWPV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:225.2857
Molecular Formula:C15H15NO
InChIKey:XGPVIJBRXABCOQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:301.5093
Molecular Formula:C21H35N
InChIKey:YKIGATXWNRKODP-KQBFAJRKSA-N
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Compound Information
Molecular Weight:233.3062
Molecular Formula:C14H19NO2
InChIKey:HWDNZLIVCGDZFU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:352.4269
Molecular Formula:C21H24N2O3
InChIKey:GRTOGORTSDXSFK-BMYCAMMWSA-N
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Compound Information
Molecular Weight:37.833
Molecular Formula:BH4Na
InChIKey:YOQDYZUWIQVZSF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:338.4433
Molecular Formula:C21H26N2O2
InChIKey:HVESDSXDWBFBHK-OOVCCDCVSA-N
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Compound Information
Molecular Weight:242.3162
Molecular Formula:C15H18N2O
InChIKey:LBNBQTTWZYYOGJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:282.4231
Molecular Formula:C19H26N2
InChIKey:ZWEWXIMUCMXDQH-MSYFUGIWSA-N
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Compound Information
Molecular Weight:256.3428
Molecular Formula:C16H20N2O
InChIKey:DDJOYOMHKDFQJK-UCNFSOMLSA-N
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Compound Information
Molecular Weight:278.3468
Molecular Formula:C15H22N2O3
InChIKey:WYRJNBRLAFQCFL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:288.4244
Molecular Formula:C19H28O2
InChIKey:ISBMAMQUENYYPA-VLUPQCQJSA-N
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Compound Information
Molecular Weight:298.3795
Molecular Formula:C18H22N2O2
InChIKey:UUAZEMSYTSTWTD-IRXDYDNUSA-N
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Compound Information
Molecular Weight:352.4269
Molecular Formula:C21H24N2O3
InChIKey:NFUNVPXUVUEVKF-JHTVJJQXSA-N
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Compound Information
Molecular Weight:207.2704
Molecular Formula:C15H13N
InChIKey:IAHXHHUHYJNKJP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:314.3789
Molecular Formula:C18H22N2O3
InChIKey:KYJBJNXQICOWAL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:199.2484
Molecular Formula:C13H13NO
InChIKey:FFUTVENPALVZID-UHFFFAOYSA-N
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Compound Information
Molecular Weight:357.4482
Molecular Formula:C23H23N3O
InChIKey:JDRSFEXPKQHCNS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:212.2902
Molecular Formula:C14H16N2
InChIKey:QVWYIZOCXPJWIZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:343.804
Molecular Formula:C19H18ClNO3
InChIKey:YQQUZFJPBFQXSY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:350.411
Molecular Formula:C21H22N2O3
InChIKey:BXTHVTLKWJZGAA-LFVXAEFHSA-N
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Compound Information
Molecular Weight:294.3908
Molecular Formula:C19H22N2O
InChIKey:YXXIRYIEQNZFNH-VFVRVIDISA-N
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Compound Information
Molecular Weight:261.3178
Molecular Formula:C18H15NO
InChIKey:FHRIBVNREMQDMC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:263.3321
Molecular Formula:C15H21NO3
InChIKey:VGQRTLUSTBGWLP-UHFFFAOYSA-N
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