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  1. World Encyclopedia
  2. Benzomorphan - Wikipedia
Benzomorphan - Wikipedia
From Wikipedia, the free encyclopedia
Benzomorphan
Names
IUPAC name
6,7-Benzomorphan
Other names
  • 1,2,3,4,5,6-Hexahydro-2,6-methano-3-benzazocine<
  • 10-Azatricyclo[7.3.1.0~2,7~]trideca-2,4,6-triene
Identifiers
CAS Number
  • 575-19-9 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 158637 ☒N
PubChem CID
  • 182394
UNII
  • A8J3S2MS1D checkY
CompTox Dashboard (EPA)
  • DTXSID80982138 Edit this at Wikidata
InChI
  • InChI=1S/C12H15N/c1-2-4-12-9(3-1)7-11-8-10(12)5-6-13-11/h1-4,10-11,13H,5-8H2 ☒N
    Key: NSLKFRGZLUIUKO-UHFFFAOYSA-N ☒N
  • InChI=1/C12H15N/c1-2-4-12-9(3-1)7-11-8-10(12)5-6-13-11/h1-4,10-11,13H,5-8H2
    Key: NSLKFRGZLUIUKO-UHFFFAOYAF
SMILES
  • C1CNC2CC1C3=CC=CC=C3C2
Properties
Chemical formula
C12H15N
Molar mass 173.259 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references
Chemical compound

Benzomorphan is a chemical compound that is the base for a series of drugs which variably act on the sigma receptors and κ-opioid receptors, including the following compounds:

  • 5,9-DEHB
  • 8-CAC
  • Alazocine
  • Anazocine
  • Bremazocine
  • Butinazocine
  • Carbazocine
  • Cogazocine
  • Cyclazocine
  • Dezocine
  • Eptazocine (Homobenzomorphan)
  • Etazocine
  • Ethylketocyclazocine
  • Fluorophen
  • Gemazocine
  • Gpa-1657 [14578-59-7][1]
  • GPA 1658 HCl salt: [26862-29-3][2]
  • GPA-208
  • GPA-3154 Fb: [35758-34-0] HCl salt: [35758-32-8]
  • Ibazocine
  • ID-1229 [56390-16-0][3][4][5]
  • LP-1[6]
  • Ketazocine
  • Metazocine
  • Moxazocine
  • Mr2266 [56649-76-4]
  • MR-2034, MR-2033-CL [57236-85-8]
  • Pentazocine
  • Phenazocine
  • Quadazocine
  • Thiazocine[citation needed]
  • Tonazocine
  • Volazocine
  • Zenazocine

Some of these agents are used as analgesics, including pentazocine, phenazocine, dezocine, and eptazocine.[7][8]

See also

[edit]
  • Benzazocine
  • Azocine
  • Morphinan

References

[edit]
  1. ^ Yokoyama, Naokata; Almaula, Prabodh I.; Block, Fred B.; Granat, Frank R.; Gottfried, Norman; Hill, Ronald T.; McMahon, Elihu H.; Munch, Walter F.; Rachlin, Howard (1979). "Syntheses, analgetic activity and physical dependence capacity of 5-phenyl-6,7-benzomorphan derivatives". Journal of Medicinal Chemistry. 22 (5): 537–553. doi:10.1021/jm00191a016. PMID 37335.
  2. ^ Yokoyama, Naokata; Block, Fred B.; Clarke, Frank H. (1970). "1,2,3,4,5,6-Hexahydro-6-phenyl-2,6-methano-3-benzazocines. II". Journal of Medicinal Chemistry. 13 (3): 488–492. doi:10.1021/jm00297a034.
  3. ^ Castañer, J.; Paton, D. M. (1978). "ID-1229". Drugs of the Future. 3 (4): 298. doi:10.1358/dof.1978.003.04.65215. ISSN 0377-8282. Retrieved 21 October 2025.
  4. ^ Yamamoto H, Saito C, Inaba S, Inukai T, Kobayashi K (May 1975). "The synthesis and pharmacology of a new analgesic, ID-1229". Arzneimittel-Forschung. 25 (5): 795–801. doi:10.1002/chin.197534266. PMID 1242327.
  5. ^ Yamamoto, H, Saito, C, Inaba, S, Inukai, T, Kobayashi, K, Fukumaru, T, Koga, Y, Homma, T, Asami, Y (26 August 1975). "ChemInform Abstract: THE SYNTHESIS AND PHARMACOLOGY OF A NEW ANALGESIC, ID-1229". Chemischer Informationsdienst. 6 (34) chin.197534266. doi:10.1002/chin.197534266. ISSN 0009-2975. PMID 1242327. Retrieved 21 October 2025.
  6. ^ Parenti, Carmela; Turnaturi, Rita; Aricò, Giuseppina; Marrazzo, Agostino; Prezzavento, Orazio; Ronsisvalle, Simone; Scoto, Giovanna M.; Ronsisvalle, Giuseppe; Pasquinucci, Lorella (2012). "Antinociceptive profile of LP1, a non-peptide multitarget opioid ligand". Life Sciences. 90 (25–26): 957–961. doi:10.1016/j.lfs.2012.04.041. PMID 22580287.
  7. ^ Kar, Ashutosh (2005). Medicinal Chemistry. New Age International. ISBN 978-81-224-1565-0.
  8. ^ Cittern PA, Kapoor VK, Parfitt RT (October 1986). "Preparation and analgesic activity of (−)-11 alpha-substituted 1,2,3,4,5,6-hexahydro-6 alpha,7-(methyleneoxy)-2,6-methano-3-benzazocines". Journal of Medicinal Chemistry. 29 (10): 1929–33. doi:10.1021/jm00160a022. PMID 2876100.
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Chemical classes of psychoactive drugs
Stimulants
  • Amphetamine-type/dopamine releasing agents: Alkylamines
    • Cycloalkylaminopropanes
  • Arylpiperazines
    • Benzylpiperazines
    • Phenylpiperazines
  • Phenethylamines
    • Aminorexes/phenyloxazolamines
    • Amphetamines/α-methylphenethylamines
      • Cathinones/β-ketoamphetamines
      • β-Hydroxyamphetamines/cathinols
      • Naphthylaminopropanes
      • Phentermines
      • Phenylisobutylamines/α-ethylphenethylamines
      • α-Propylphenethylamines
    • Phenylmorpholines/phenmetrazines
  • Thiopropamines/thienylaminopropanes
  • Cocaine-type/typical dopamine reuptake inhibitors: Phenethylamines
    • Phenidates/benzylpiperidines
    • Phenylethylpyrrolidines
      • Pyrrolidinophenones
  • Phenyltropanes/cocaine analogues
  • Modafinil-type/atypical dopamine reuptake inhibitors: Modafinil analogues
  • Phenylpiracetams
  • Caffeine-type/adenosine receptor antagonists: Xanthines/methylxanthines
  • Nicotine-type/nicotinic acetylcholine receptor agonists: Nicotine analogues
Depressants
  • GABAA receptor positive allosteric modulators: Alcohols/ethanol analogues
  • Barbiturates
  • Benzodiazepines
    • Pyrrolobenzodiazepines
    • Thienobenzodiazepines
    • Thienodiazepines
    • Thienotriazolodiazepines
    • Triazolobenzodiazepines
  • Carbamates
  • Ethers
  • Neuroactive steroids
  • Nonbenzodiazepines
    • β-Carbolines
    • Cyclopyrrolones
    • Imidazopyridines
    • Pyrazolopyrimidines
  • Phenols
  • Piperidinediones
  • Quinazolinones
  • GABAA receptor agonists: Isoxazoles
  • GHB receptor agonists: 1,4-Butanediols
  • α2δ subunit-containing voltage-gated calcium channel blockers: Gabapentinoids
  • Opioids/μ-opioid receptor agonists: Benzimidazoles
    • Nitazenes
  • Fentanyl analogues/phenylpiperidines
  • Mitragyna alkaloids
  • Morphinans/phenanthrenes
    • Opiates/opium alkaloids
  • Utopioids
  • Antihistamines/H1 receptor antagonists: Benzimidazoles
  • Diarylmethanes
  • Ethylenediamines
  • Tricyclics
    • Dibenzocycloheptenes
Hallucinogens
  • Serotonergic psychedelics/serotonin 5-HT2A receptor agonists: Arylpiperazines
    • Phenylpiperazines
    • Quinolinylpiperazines
  • Cyclized phenethylamines
    • 3-Benzazepines
  • Cyclized tryptamines
    • Azepinoindoles
      • Ibogalogs
      • Iboga alkaloids
    • β-Carbolines
      • Harmala alkaloids
    • Ergolines
      • Lysergamides
    • Simplified/partial lysergamides
  • Phenethylamines (methoxyphenethylamines)
    • 2Cs
      • 25-NB/NBOMes
      • 2C-Os
      • 2C-Ts
        • HOT-x
      • TWEETIOs
    • Amphetamines/α-methylphenethylamines
      • 3Cs
      • Dimethoxyamphetamines/DMAs
      • DOx
        • Alephs
      • Ethylenedioxyamphetamines/EDxx
      • Methylenedioxyamphetamines/MDxx
      • Trimethoxyamphetamines/TMAs
    • BOx
    • FLYs/benzofurans
    • Phenylisobutylamines/α-ethylphenethylamines
      • 4Cs
    • Scalines
    • Ψ-PEAs
  • Tryptamines
    • α-Alkyltryptamines
      • α-Alkyl-β-ketotryptamines
    • 4-Hydroxytryptamines
    • 5-Hydroxytryptamines
      • 5-Methoxytryptamines
  • Miscellaneous
  • Dissociatives/NMDA receptor antagonists: Adamantanes
  • Arylcyclohexylamines
  • Diarylethylamines
  • Morphinans
  • κ-Opioid receptor agonists: Benzomorphans
  • Salvinorins
  • GABAA receptor agonists: Isoxazoles
  • Deliriants/anticholinergics/muscarinic acetylcholine receptor antagonists: Diarylmethanes
  • Tropanes
  • Others: Cyclized tryptamines
    • Azepinoindoles
      • Iboga alkaloids
  • (Phyto)cannabinoids
Entactogens
  • Serotonin releasing agents: Phenethylamines
    • 2-Aminoindanes
    • 2-Aminotetralins
    • Amphetamines
      • Benzofuranylaminopropanes
      • Benzothiophenylaminopropanes
      • Ethylenedioxyamphetamines/EDxx
      • Indanylaminopropanes
      • Indolylaminopropanes
      • Methylenedioxyamphetamines/MDxx
      • Tetralinylaminopropanes
  • Tryptamines
    • α-Alkyltryptamines
  • Miscellaneous
Psychiatric drugs
  • Anxiolytics: Azapirones
  • Benzodiazepines
    • Pyrrolobenzodiazepines
    • Thienobenzodiazepines
    • Thienodiazepines
    • Thienotriazolodiazepines
    • Triazolobenzodiazepines
  • Antidepressants: Tricyclic antidepressants
    • Dibenzazepines
    • Dibenzocycloheptenes
    • Dibenzothiepins
    • Dibenzoxazepines
    • Dibenzoxepins
  • Tetracyclic antidepressants
  • Antipsychotics/dopamine D2 receptor antagonists or partial agonists: Benzamides
  • Benzimidazoles
  • Benzisothiazoles
  • Benzisoxazoles
  • Butyrophenones
  • Diphenylbutylpiperidines
  • Phenylpiperazines
  • Tricyclics
    • Dibenzazepines
    • Dibenzodiazepines
    • Dibenzothiazepines
    • Dibenzothiepins
    • Dibenzoxazepines
    • Phenothiazines
    • Thienobenzodiazepines
  • Mood stabilizers/anticonvulsants: Gabapentinoids
  • Tricyclics
    • Dibenzazepines
  • Valproates
Others
  • Nootropics: Racetams
    • Phenylpiracetams
  • Miscellaneous: 3-Benzazepines
  • Adamantanes
  • Catecholamines
  • Tetrahydroisoquinolines
  • Yohimbans


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