ALPHAPRODINE

US Previously Marketed

First approved in 1949

Details

Stereochemistry	RACEMIC
Molecular Formula	C16H23NO2
Molecular Weight	261.3593
Optical Activity	( + / - )
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCC(=O)O[C@@]1(CCN(C)C[C@@H]1C)C2=CC=CC=C2

InChI

InChIKey=UVAZQQHAVMNMHE-XJKSGUPXSA-N

InChI=1S/C16H23NO2/c1-4-15(18)19-16(14-8-6-5-7-9-14)10-11-17(3)12-13(16)2/h5-9,13H,4,10-12H2,1-3H3/t13-,16+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C16H23NO2
Molecular Weight	261.3593
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/mesh/68000522 | https://www.ncbi.nlm.nih.gov/pubmed/13163471 | https://www.ncbi.nlm.nih.gov/pubmed/13444352

ALPHAPRODINE is an opioid analgesic. It was used in obstetrics, as pre-operative medication, and for minor surgical procedures. In addition, this drug was used in the dentistry setting to help effectively manage pain associated with dental procedures.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 619 Sources: https://www.ncbi.nlm.nih.gov/pubmed/13163471 https://jamanetwork.com/journals/jama/article-abstract/320530	Primary		Not Provided 511	Nisentil Approved Use Unknown

AUC

Value	Dose	Co-administered	Analyte	Population
50.08 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7358866	35 mg/kg bw single, intravenous dose: 35 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:		ALPHAPRODINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
4.6 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7358866	35 mg/kg bw single, intravenous dose: 35 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:		ALPHAPRODINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Sourcing

Vendor/Aggregator	ID	URL
BioBlocks	A2324/0098038
Compound Cloud	BCC0091630
HongKong Chemhere	SCD28993
Lab Network	LN03026904
mcule	MCULE-1052845766
mcule	MCULE-7919657032
NCI Plated 2007	117858
Toronto Research Chemicals	KIT8965
Toronto Research Chemicals	P755300
ZINC	ZINC000001087483	http://zinc15.docking.org/substances/ZINC000001087483

PubMed

Title	Date	PubMed
[Three auxiliary medications in obstetrics. 1955].	2010-11	21299003
Structure determination of neoefrapeptins A to N: peptides with insecticidal activity produced by the fungus Geotrichum candidum.	2006-05	16883776
Local anesthesia and narcotic drug interaction in pediatric dentistry.	1988-01-01	3422794
Ketamine-pancuronium-narcotic technic for cardiovascular surgery in infants--a comparative study.	1975-11-01	1239221
The combined use of alphaprodine (nisentil) hydrochloride and levallorphan (lorfan) tartrate for analgesia in obstetrics.	1957-08	13444352
Use of Nisentil hydrochloride as an analgesic agent during cystoscopic procedures.	1954-04	13163471

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:45:43 GMT 2025` Edited by `admin` on `Mon Mar 31 17:45:43 GMT 2025`
Record UNII	001O2254AC
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ALPHAPRODINE

Official Name

English

IDS-NA-011

Preferred Name

English

ACSCN-9010

Common Name

English

alphaprodine [INN]

Common Name

English

DL-.ALPHA.-PRODINE

Common Name

English

ALPHAPRODINE [HSDB]

Common Name

English

NISINTIL

Common Name

English

.ALPHA.-1,3-DIMETHYL-4-PHENYL-4-PROPIONOXYPIPERIDINE

Common Name

English

(±)-1,3-DIMETHYL-4-PHENYL-4-PIPERIDINOL PROPIONATE (ESTER)

Common Name

English

PRISILIDIN

Common Name

English

ALPHAPRODINE [MI]

Common Name

English

ALPHAPRODINE [VANDF]

Common Name

English

Alphaprodine [WHO-DD]

Common Name

English

4-PIPERIDINOL, 1,3-DIMETHYL-4-PHENYL-, PROPANOATE (ESTER), CIS-(±)-

Common Name

English

Classification Tree Code System Code

DEA NO.

9010