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    Pentazocine

    ACTIVE PHARMA INGREDIENTS

    INTERMEDIATES

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    2D Structure
    Also known as: 17146-95-1, Pentazocine lactate [usan], 1p2xib510o, (1r,9r,13r)-1,13-dimethyl-10-(3-methylbut-2-enyl)-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-4-ol;2-hydroxypropanoic acid, (2r*,6r*,11r*)-1,2,3,4,5,6-hexahydro-6,11-dimethyl-3-(3-methyl-2-butenyl)-2,6-methano-3-benzazocin-8-ol lactate (salt), Talwin (lactate)
    Molecular Formula
    C22H33NO4
    Molecular Weight
    375.5  g/mol
    InChI Key
    QNLDTXPVZPRSAM-DTOXXUQYSA-N
    FDA UNII
    1P2XIB510O
    The first mixed agonist-antagonist analgesic to be marketed. It is an agonist at the kappa and sigma opioid receptors and has a weak antagonist action at the mu receptor. (From AMA Drug Evaluations Annual, 1991, p97)
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (1R,9R,13R)-1,13-dimethyl-10-(3-methylbut-2-enyl)-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-4-ol;2-hydroxypropanoic acid
    2.1.2 InChI
    InChI=1S/C19H27NO.C3H6O3/c1-13(2)7-9-20-10-8-19(4)14(3)18(20)11-15-5-6-16(21)12-17(15)19;1-2(4)3(5)6/h5-7,12,14,18,21H,8-11H2,1-4H3;2,4H,1H3,(H,5,6)/t14-,18+,19+;/m0./s1
    2.1.3 InChI Key
    QNLDTXPVZPRSAM-DTOXXUQYSA-N
    2.1.4 Canonical SMILES
    CC1C2CC3=C(C1(CCN2CC=C(C)C)C)C=C(C=C3)O.CC(C(=O)O)O
    2.1.5 Isomeric SMILES
    C[C@H]1[C@H]2CC3=C([C@@]1(CCN2CC=C(C)C)C)C=C(C=C3)O.CC(C(=O)O)O
    2.2 Other Identifiers
    2.2.1 UNII
    1P2XIB510O
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Fortral

    2. Hydrochloride, Pentazocine

    3. Lactate, Pentazocine

    4. Lexir

    5. Pentazocine

    6. Pentazocine Hydrochloride

    7. Talwin

    2.3.2 Depositor-Supplied Synonyms

    1. 17146-95-1

    2. Pentazocine Lactate [usan]

    3. 1p2xib510o

    4. (1r,9r,13r)-1,13-dimethyl-10-(3-methylbut-2-enyl)-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-4-ol;2-hydroxypropanoic Acid

    5. (2r*,6r*,11r*)-1,2,3,4,5,6-hexahydro-6,11-dimethyl-3-(3-methyl-2-butenyl)-2,6-methano-3-benzazocin-8-ol Lactate (salt)

    6. Talwin (lactate)

    7. Pentalgine

    8. Talwin (as Lactate)

    9. Unii-1p2xib510o

    10. Talwin Injection

    11. Einecs 241-209-9

    12. Einecs 304-943-1

    13. Talwin (tn)

    14. Pentazocine Lactate (usp)

    15. Schembl42094

    16. (all-r)-pentazocine Dl-lactate

    17. Chembl1200327

    18. Pentazocine Lactate [mi]

    19. Dtxsid101027503

    20. Pentazocine Lactate [vandf]

    21. Pentazocine Lactate [mart.]

    22. Pentazocine Lactate [who-dd]

    23. Pentazocine Lactate [green Book]

    24. Pentazocine Lactate [orange Book]

    25. 2-hydroxypropanoic Acid Compd. With (2alpha,6alpha,11r*)-1,2,3,4,5,6-hexahydro-6,11-dimethyl-3-(3-methyl-2-butenyl)-2,6-methanol-3-benzocin-8-ol (1:1)

    26. Lactic Acid, Compd. With 1,2,3,4,5,6-hexahydro-6,11-dimethyl-3-(3-methyl-2-butenyl)-2,6-methano-3-benzazocin-8-ol (1:1)

    27. Lactic Acid, Compound With (2alpha,6alpha,11r*)-1,2,3,4,5,6-hexahydro-6,11-dimethyl-3-(3-methylbut-2-enyl)-2,6-methano-3-benzocin-8-ol (1:1)

    28. Pentazocine Lactate [ep Monograph]

    29. D02111

    30. Q27252701

    31. 2,6-methano-3-benzazocin-8-ol, 1,2,3,4,5,6-hexahydro-6,11-dimethyl-3-(3-methyl-2-butenyl)-, (2.alpha.,6.alpha.,11r*)-, Compd. With 2-hydroxypropanoic Acid (1:1)

    32. 2,6-methano-3-benzazocin-8-ol, 1,2,3,4,5,6-hexahydro-6,11-dimethyl-3-(3-methyl-2-butenyl)-, (2alpha,6alpha,11r*)-, Compd. With 2-hydroxypropanoic Acid (1:1)

    33. Propanoic Acid, 2-hydroxy-, Compd. With (2alpha,6alpha,11r*)-1,2,3,4,5,6-hexahydro-6,11-dimethyl-3-(3-methyl-2-butenyl)-2,6-methanol-3-benzocin-8-ol (1:1)

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 375.5 g/mol
    Molecular Formula C22H33NO4
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count3
    Exact Mass375.24095853 g/mol
    Monoisotopic Mass375.24095853 g/mol
    Topological Polar Surface Area81 Ų
    Heavy Atom Count27
    Formal Charge0
    Complexity473
    Isotope Atom Count0
    Defined Atom Stereocenter Count3
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Pharmacology and Biochemistry
    4.1 MeSH Pharmacological Classification

    Adjuvants, Anesthesia

    Agents that are administered in association with anesthetics to increase effectiveness, improve delivery, or decrease required dosage. (See all compounds classified as Adjuvants, Anesthesia.)

    Analgesics, Opioid

    Compounds with activity like OPIATE ALKALOIDS, acting at OPIOID RECEPTORS. Properties include induction of ANALGESIA or NARCOSIS. (See all compounds classified as Analgesics, Opioid.)

    Narcotic Antagonists

    Agents inhibiting the effect of narcotics on the central nervous system. (See all compounds classified as Narcotic Antagonists.)

    Narcotics

    Agents that induce NARCOSIS. Narcotics include agents that cause somnolence or induced sleep (STUPOR); natural or synthetic derivatives of OPIUM or MORPHINE or any substance that has such effects. They are potent inducers of ANALGESIA and OPIOID-RELATED DISORDERS. (See all compounds classified as Narcotics.)