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P127

Sigma-Aldrich

(+)-Pentazocine

solid

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Empirical Formula (Hill Notation):
C19H27NO
CAS Number:
7361-76-4
Molecular Weight:
285.42
UNSPSC Code:
12352200
PubChem Substance ID:
24898179
NACRES:
NA.77

form

solid

Quality Level

100

optical activity

[α]23/D +134.6°, c = 1 in chloroform(lit.)

drug control

USDEA Schedule IV; Home Office Schedule 3; stupéfiant (France); kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada; psicótropo (Spain); Decreto Lei 15/93: Tabela IIC (Portugal)

color

white

originator

Sanofi Aventis

SMILES string

[H][C@@]12Cc3ccc(O)cc3[C@@](C)(CCN1C\C=C(\C)C)[C@@H]2C

InChI

1S/C19H27NO/c1-13(2)7-9-20-10-8-19(4)14(3)18(20)11-15-5-6-16(21)12-17(15)19/h5-7,12,14,18,21H,8-11H2,1-4H3/t14-,18+,19+/m1/s1

InChI key

VOKSWYLNZZRQPF-CCKFTAQKSA-N

Gene Information

human ... EBP(10682)
rat ... Chrm1(25229) , Chrm2(81645) , Drd2(24318) , Oprm1(25601)

Biochem/physiol Actions

σ receptor agonist; active enantiomer of pentazocine.

Features and Benefits

This compound was developed by Sanofi Aventis. To browse the list of other pharma-developed compounds, Approved Drugs, and Drug Candidates, click here.

Caution

Photosensitive

Reconstitution

A 10 mM solution of (+)-pentazocine is prepared by warming 28.5 mg of (+)-pentazocine free base in 2 mL of 0.1N HCl with shaking or sonication. When all solids have dissolved, the solution is cooled to room temperature and diluted with 10 mL of pH 7 buffer. Solutions should be freshly prepared, since cooling below room temperature may result in precipitation.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302 + H312 + H332

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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G F Steinfels et al.
Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology, 1(4), 321-327 (1988-12-01)
Research on the sigma receptor, a binding site associated with drug-induced psychotomimetic behaviors, has been hampered because most sigma agonists also interact with the phencyclidine (PCP) receptor. (+)-Pentazocine, a human psychotogen, is a selective sigma receptor ligand. To demonstrate sigma
Mayada Said et al.
Colloids and surfaces. B, Biointerfaces, 170, 258-265 (2018-06-24)
Agomelatine suffers from extensive inactivation through 1st pass effect with a limited oral bioavailability (5%). The aim of this study was to formulate and optimize liquid nanocrystals (LNC) containing agomelatine to enhance the transdermal permeation of the drug. The independent
Rania Hamed et al.
International journal of pharmaceutics, 570, 118684-118684 (2019-09-11)
The aim of this study was to develop an ibuprofen microemulsion (IBU-ME) incorporated into in situ gels (microgels) for local delivery into periodontal pockets. The IBU-ME was prepared at a concentration of 1% w/v IBU. Various concentrations of the thermosensitive
S Stevens Negus et al.
Pharmacological reviews, 66(3), 869-917 (2014-06-29)
Intracranial self-stimulation (ICSS) is a behavioral procedure in which operant responding is maintained by pulses of electrical brain stimulation. In research to study abuse-related drug effects, ICSS relies on electrode placements that target the medial forebrain bundle at the level
Brett H Mueller et al.
Experimental eye research, 128, 156-169 (2014-10-12)
Sigma-1 receptor (σ-1) activation and mitogen-activated protein kinases (MAPKs) have been shown to protect retinal ganglion cells (RGCs) from cell death. The purpose of this study was to determine if σ-1 receptor stimulation with pentazocine could promote neuroprotection under conditions
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