(+)-Pentazocine

Base Information

• Chemical Name: (+)-Pentazocine
• CAS No.: 359-83-1
• Deprecated CAS: 58501-97-6
• Molecular Formula: C19H27 N O
• Molecular Weight: 285.429
• Hs Code.: 2933330000
• European Community (EC) Number: 635-312-1
• UNII: A2G9VU2P2J
• ChEMBL ID: CHEMBL60542
• DSSTox Substance ID: DTXSID90870517
• Metabolomics Workbench ID: 143372
• Nikkaji Number: J356.522J
• Pharos Ligand ID: GPD2C2FH4PZJ,GPDHKF9UX1CY
• Wikidata: Q27273533
• Mol file: 359-83-1.mol

Synonyms:(+)-Pentazocine;d-Pentazocine;(+)-cis-Pentazocine;Pentazocine, D-;Pentazocine, (+)-;7361-76-4;(+)-alpha-Pentazocine;UNII-A2G9VU2P2J;A2G9VU2P2J;Pentazocine 2S,6S,11S-form [MI];CHEMBL60542;(-)-PENTAZOCINE;2,6-Methano-3-benzazocin-8-ol, 1,2,3,4,5,6-hexahydro-6,11-dimethyl-3-(3-methyl-2-buten-1-yl)-, (2S,6S,11S)-;(+)-[3H]-Pentazocine;[3H]-(+)-Pentazocine;CHEMBL2311194;(2S,6S,11S)-6,11-dimethyl-3-(3-methylbut-2-en-1-yl)-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocin-8-ol;(+)-pen-tazocine;(+)-Pentazocine, solid;SCHEMBL4461209;DTXSID90870517;(+)-.ALPHA.-PENTAZOCINE;(2R,6R,11R)-6,11-Dimethyl-3-(3-methyl-but-2-enyl)-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-ol;(6R,11S)-6,11-Dimethyl-3-(3-methyl-but-2-enyl)-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-ol;6,11-Dimethyl-3-(3-methyl-but-2-enyl)-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-ol;BDBM50035131;BDBM50423875;PDSP2_001657;(-)-Pentazocine, >=98% (HPLC);Q27273533;(+)-(6R,11S)-6,11-dimethyl-3-(3-methyl-but-2-enyl)-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-ol;(1S,9S,13S)-1,13-dimethyl-10-(3-methylbut-2-enyl)-10-azatricyclo[7.3.1.0~2,7~]trideca-2,4,6-trien-4-ol;(2R,6R,11S)-6,11-dimethyl-3-(3-methyl-but-2-enyl)-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-ol;(2S,3R,6S,11S)-6,11-Dimethyl-3-(3-methyl-but-2-enyl)-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-ol;(2S,6S,11S)-6,11-Dimethyl-3-(3-methyl-but-2-enyl)-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-ol;6,11-Dimethyl-3-(3-methyl-but-2-enyl)-1,2,3,4,5,6-hexahydro-2,6-ethano-benzo[d]azocin-8-ol(+)-pentazocine;6,11-Dimethyl-3-(3-methyl-but-2-enyl)-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-ol ((+)-Pentazocine);6,11-Dimethyl-3-(3-methyl-but-2-enyl)-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-ol anion;6,11-Dimethyl-3-(3-methyl-but-2-enyl)-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-ol((+)pentazocine)

 This product is a nationally controlled contraband, and the Lookchem platform doesn't provide relevant sales information.

Chemical Property of (+)-Pentazocine

Chemical Property:

• Appearance/Colour: Crystalline Solid
• Vapor Pressure: 4.35E-07mmHg at 25°C
• Melting Point: 145.4-147.20ºC
• Refractive Index: 1.5180 (estimate)
• Boiling Point: 403.5°C at 760 mmHg
• PKA: pKa 8.68±0.05;11.23± 0.05(H2O,t =20,I=0.1) (Uncertain)
• Flash Point: 180.8°C
• PSA: 23.47000
• Density: 1.036g/cm³
• LogP: 3.82050
• Storage Temp.: Controlled Substance, -20?C Freezer
• Solubility.: DMSO: >10mg/mL
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 285.209264485
• Heavy Atom Count: 21
• Complexity: 414

Purity/Quality:

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,T,F
• Statements: 22-39/23/24/25-23/24/25-11
• Safety Statements: 7-16-36/37-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1C2CC3=C(C1(CCN2CC=C(C)C)C)C=C(C=C3)O
• Isomeric SMILES: C[C@@H]1[C@@H]2CC3=C([C@]1(CCN2CC=C(C)C)C)C=C(C=C3)O
• Uses: (?)-Pentazocine is a benzomorphan-type opiate with analgesic properties. It binds to opioid receptors (Ki values = 7.2, 31, and 5.7 nM for κ-, δ-, μ-opioid receptors, respectively) and to the type 1 σ-receptor (Kd = 12 nM). (?)-Pentazocine is abused with methylphenidate and other drugs. It is regulated as a Schedule IV compound in the United States. This product is intended for forensic and research applications. Mixed opioid agonist-antagonist. Controlled substance. Analgesic (narcotic).
• Therapeutic Function: Analgesic

Technology Process of (+)-Pentazocine

There total 30 articles about (+)-Pentazocine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

O-methyl pentazocine (577991-78-7) → pentazocin (359-83-1,7313-83-9,7361-76-4,7488-49-5,21820-34-8,39188-58-4,55643-30-6,75257-91-9,146565-86-8)

Guidance literature:

With sodium thioethylate; In N,N-dimethyl-formamide; at 130 ℃; for 5h;

DOI:10.1021/ja0360539

Reference yield: 86.1%

(2R,6R,11R)-6,11-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-ol (16603-67-1) + prenyl bromide (870-63-3) → pentazocin (359-83-1,7313-83-9,7361-76-4,7488-49-5,21820-34-8,39188-58-4,55643-30-6,75257-91-9,146565-86-8)

Guidance literature:

With triethylamine; In 1-methyl-pyrrolidin-2-one; at 40 - 45 ℃; for 6h;

Reference yield:

1-methyl-7-methoxy-2-tetralone (1204-23-5) → pentazocin (359-83-1,7313-83-9,7361-76-4,7488-49-5,21820-34-8,39188-58-4,55643-30-6,75257-91-9,146565-86-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: (η³-C3H5PdCl)2; (R,R)-bridged dihydroanthracene derivative ligand; Cs2CO3 / 1,2-dimethoxy-ethane / 0.25 h / 20 °C

1.2: 1,2-dimethoxy-ethane / 0.08 h / 20 °C

2.1: 98 percent / t-BuOK / tetrahydrofuran / 20 °C

3.1: 82 percent / NMO; aq. OsO₄ / tetrahydrofuran / 5 h / 20 °C

4.1: 92 percent / aq. NaIO₄ / tetrahydrofuran / 1 h / 20 °C

5.1: MgSO₄ / tetrahydrofuran; methanol / 20 °C

5.2: 85 percent / NaBH₄ / tetrahydrofuran; methanol / 1 h

6.1: 100 percent / iPr₂NH; tetramethylenediamine; n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C

7.1: 94 percent / NaSEt / dimethylformamide / 5 h / 130 °C

With sodium periodate; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; bis(η3-allyl-μ-chloropalladium(II)); N,N,N,N,-tetramethylethylenediamine; (R,R)-bridged dihydroanthracene derivative ligand; potassium tert-butylate; magnesium sulfate; caesium carbonate; diisopropylamine; sodium thioethylate; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; hexane; N,N-dimethyl-formamide; 2.1: Wittig olefination;

DOI:10.1021/ja0360539

upstream raw materials:

(-)-cis-N-Normetazocine

prenyl bromide

O-methyl pentazocine

1-methyl-7-methoxy-2-tetralone

Downstream raw materials:

Thiobenzoic acid S-[(6R,11R)-6,11-dimethyl-3-(3-methyl-but-2-enyl)-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-yl] ester

Thiobenzoic acid S-[(2R,6R,11R)-6,11-dimethyl-3-(3-methyl-but-2-enyl)-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-yl] ester

Refernces

• 1、 -. "Pentazocine prodrug as well as preparation method and application thereof". . . Retrieved 2020/07/15.
• 2、 Yang, Xiaobao,Zhai, Hongbin,Li, Zhong. "Enantiocontrolled synthesis of (-)-9-epi-pentazocine and (-)-aphanorphine". supporting information; experimental part. p. 2457 - 2460. Retrieved 2009/05/26.