NAPITANE

Details

Stereochemistry	RACEMIC
Molecular Formula	C22H25NO2
Molecular Weight	335.4394
Optical Activity	( + / - )
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C([C@@H]1CCCC2=C3OCOC3=CC=C12)N4CC[C@@H](C4)C5=CC=CC=C5

InChI

InChIKey=HAEPGZUGYMHCJE-ROUUACIJSA-N

InChI=1S/C22H25NO2/c1-2-5-16(6-3-1)17-11-12-23(13-17)14-18-7-4-8-20-19(18)9-10-21-22(20)25-15-24-21/h1-3,5-6,9-10,17-18H,4,7-8,11-15H2/t17-,18-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C22H25NO2
Molecular Weight	335.4394
Charge	0
Count

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

Description
Sources: https://adisinsight.springer.com/drugs/800005107 | https://www.ncbi.nlm.nih.gov/pubmed/8525465

Napitane [A 75200, ABT 200] is a norepinephrine uptake inhibitor and α2 adrenoceptor antagonist. It was undergoing clinical trials with Abbott in the USA as a treatment for depression. However it was discontinued later. Napitane is a potent alpha 2-adrenoceptor antagonist (Ki = 1.2 nM) with modest norepinephrine uptake-blocking activity (IC50 = 841 nM).

Originator

Approval Year

PubMed

Title	Date	PubMed
Effects of the putative antidepressant, ABT 200, on the clearance of exogenous norepinephrine in rat cerebellum.	1995-09	8525465
ABT-200, a norepinephrine uptake inhibitor, blocks Ca2+ signals in chromaffin cells.	1994-10-14	7851493
Actions of A-75200, a novel catecholamine uptake inhibitor, on norepinephrine uptake and release from bovine adrenal chromaffin cells.	1993-03	8450458

Sample Use Guides

In Vivo Use Guide

Rats: 30 mg/kg i.p.

Route of Administration: Intraperitoneal

In Vitro Use Guide

Napitane is a potent alpha 2-adrenoceptor antagonist (Ki = 1.2 nM) with modest norepinephrine uptake-blocking activity (IC50 = 841 nM).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:39:08 GMT 2025` Edited by `admin` on `Mon Mar 31 18:39:08 GMT 2025`
Record UNII	5Y6TH3C053
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NAPITANE

Official Name

English

A-75200

Preferred Name

English

(±)-(3R*)-3-PHENYL-1-(((6R*)-6,7,8,9-TETRAHYDRONAPHTHO(1,2-D)-1,3-DIOXOL-6-YL)METHYL)PYRROLIDINE

Systematic Name

English

napitane [INN]

Common Name

English

PYRROLIDINE, 3-PHENYL-1-((6,7,8,9-TETRAHYDRONAPHTHO(1,2-D)-1,3-DIOXOL-6-YL)METHYL)-, (R*,R*)-(±)-

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29713