PHENAZOCINE, (-)-

US Previously Marketed

First approved in 1959

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H27NO
Molecular Weight	321.4559
Optical Activity	( - )
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@H]1[C@H]2CC3=CC=C(O)C=C3[C@]1(C)CCN2CCC4=CC=CC=C4

InChI

InChIKey=ZQHYKVKNPWDQSL-KNXBSLHKSA-N

InChI=1S/C22H27NO/c1-16-21-14-18-8-9-19(24)15-20(18)22(16,2)11-13-23(21)12-10-17-6-4-3-5-7-17/h3-9,15-16,21,24H,10-14H2,1-2H3/t16-,21+,22+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C22H27NO
Molecular Weight	321.4559
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25972091 | https://www.ncbi.nlm.nih.gov/pubmed/10635445 | https://www.ncbi.nlm.nih.gov/pubmed/8148469

(-)-Phenazocine is an opioid analgesic drug, which is related to pentazocine and has a similar profile of effects. (-)-Phenazocine is a potent mu opioid receptor agonist. In addition, (−)-phenazocine is also known to bind to δ opioid receptors (DOR) and κ opioid receptors (KOR). Regarding their analgesic potency, (−)-phenazocine was twenty times more potent than morphine in the hot plate test and sixty times more potent than its dextro enantiomer when it was subcutaneously (s.c.) administered

Approval Year

Doses

Dose	Population	Adverse events
6 mg single, intramuscular Highest studied dose Dose: 6 mg Route: intramuscular Route: single Dose: 6 mg Sources: https://citeseerx.ist.psu.edu/viewdoc/download?doi=10.1.1.834.2450&rep=rep1&type=pdf Page: p.338	unhealthy Health Status: unhealthy Condition: Chronic pain due to cancer Sources: https://citeseerx.ist.psu.edu/viewdoc/download?doi=10.1.1.834.2450&rep=rep1&type=pdf Page: p.338	Sources: https://citeseerx.ist.psu.edu/viewdoc/download?doi=10.1.1.834.2450&rep=rep1&type=pdf Page: p.338

Sourcing

Vendor/Aggregator	ID	URL
Compound Cloud	443405
Toronto Research Chemicals	P295400
ZINC	ZINC000001481896	http://zinc15.docking.org/substances/ZINC000001481896

PubMed

Title	Date	PubMed
Oral pentazocine and phenazocine: a comparison in postoperative pain.	1971 May	5556861
MS-377, a selective sigma receptor ligand, indirectly blocks the action of PCP in the N-methyl-D-aspartate receptor ion-channel complex in primary cultured rat neuronal cells.	2002 Feb 22	11991251
Generation and phenotypic analysis of sigma receptor type I (sigma 1) knockout mice.	2003 Oct	14622179
Sigma-1 receptors bind cholesterol and remodel lipid rafts in breast cancer cell lines.	2007 Dec 1	18056441
Involvement of the sigma1 receptor in inhibiting activity of fluvoxamine on marble-burying behavior: comparison with paroxetine.	2007 Jun 1	17349995
The C-terminal amidated analogue of the substance P (SP) fragment SP(1-7) attenuates the expression of naloxone-precipitated withdrawal in morphine dependent rats.	2009 Dec	19686790

Patents

Substance Class	Chemical Created by `admin` on `Sat Dec 16 07:56:19 GMT 2023` Edited by `admin` on `Sat Dec 16 07:56:19 GMT 2023`
Record UNII	7UZW80C91Q
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PHENAZOCINE, (-)-

Common Name

English

PHENAZOCINE CIS-(-)-FORM [MI]

Common Name

English

(-)-.ALPHA.-PHENAZOCINE

Common Name

English

2,6-METHANO-3-BENZAZOCIN-8-OL, 1,2,3,4,5,6-HEXAHYDRO-6,11-DIMETHYL-3-(2-PHENYLETHYL)-, (2R-(2.ALPHA.,6.ALPHA.,11R*))-

Systematic Name

English

(-)-PHENAZOCINE

Common Name

English

Code System Code Type Description

PUBCHEM

443405