NICOCODINE HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C24H24N2O4.ClH
Molecular Weight	440.919
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.[H][C@@]12CC3=C4C(O[C@H]5[C@@H](OC(=O)C6=CN=CC=C6)C=C[C@]1([H])[C@@]45CCN2C)=C(OC)C=C3

InChI

InChIKey=ORUPNZYTIDBXQZ-CBXNJKKFSA-N

InChI=1S/C24H24N2O4.ClH/c1-26-11-9-24-16-6-8-19(29-23(27)15-4-3-10-25-13-15)22(24)30-21-18(28-2)7-5-14(20(21)24)12-17(16)26;/h3-8,10,13,16-17,19,22H,9,11-12H2,1-2H3;1H/t16-,17+,19-,22-,24-;/m0./s1

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C24H24N2O4
Molecular Weight	404.4584
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://pdfs.semanticscholar.org/43d1/63ec173a878a14eb0fc26604851454cc747d.pdf | https://www.tandfonline.com/doi/abs/10.1080/00032718008078010?journalCode=lanl20

Nicocodine is an opioid related to codeine. It is also an antitussive agent. Nicocodine exhibits at least twice the potency of codeine in clinical experiments. The study of the pharmacokinetic behaviour of nicocodine by means of blood and brain level curves of rats after i .v. application showed that the penetration of the blood brain barrier seems to be favoured for nicocodine. The detected peak concentration of nicocodine in brain after i.v. application is 4.4 times higher than the blood level values at the same time - codeine the main metabolite is detected in almost equal amounts in brain and blood. A comparative assay of codeine and nicocodine after p.o. application of equimolar doses per kg body weight revealed that predominantly codeine is found in brain and its peak value after nicocodine administration is 3-fold higher than after codeine administration. Nicocodine is hydrolysable to morphine and the WHO Expert Committee on Addiction-Producing Drugs (1962) recommended its international control as a narcotic, like other convertible drugs in the morphine series.

CNS Activity

Approval Year

PubMed

Title	Date	PubMed
[Comparative actions of morphine, codeine and nicocodine on respiration and external pancreatic and biliary secretions in the rat].	1967 May	6040366
Reinforcing properties of nicocodine in the rhesus monkey.	1979	115478

Sample Use Guides

In Vivo Use Guide

Single doses of nicocodine of 5 or 10 mg in 27 tuberculous patients who had been receiving codeine gave similar cough relief without side-effects.

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Sat Dec 16 02:16:27 UTC 2023` Edited by `admin` on `Sat Dec 16 02:16:27 UTC 2023`
Record UNII	UD79634178
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NICOCODINE HYDROCHLORIDE

Common Name

English

(5.ALPHA.,6.ALPHA.)-7,8-DIDEHYDRO-4,5-EPOXY-3-METHOXY-17-METHYLMORPHINAN-6-YL PYRIDINE-3-CARBOXYLATE HYDROCHLORIDE

Systematic Name

English

Nicocodine hydrochloride [WHO-DD]

Common Name

English

MORPHINAN-6-OL, 7,8-DIDEHYDRO-4,5-EPOXY-3-METHOXY-17-METHYL-, 3-PYRIDINECARBOXYLATE (ESTER), MONOHYDROCHLORIDE, (5.ALPHA.,6.ALPHA.)-

Systematic Name

English

Code System Code Type Description

ECHA (EC/EINECS)

261-194-2