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B138

Sigma-Aldrich

BTCP hydrochloride

Synonym(s):

Benocyclidine hydrochloride, N-[1-(Benzo[b]thien-2-yl-cyclohexyl)]piperidine hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C19H25NS · HCl
CAS Number:
112726-66-6
Molecular Weight:
335.93
MDL number:
MFCD00153777
UNSPSC Code:
12352200
PubChem Substance ID:
24278283
NACRES:
NA.77

form

powder

drug control

regulated under CDSA - not available from Sigma-Aldrich Canada

color

white

solubility

H2O: >180 mg/mL
ethanol: soluble

storage temp.

2-8°C

SMILES string

Cl[H].C1CCN(CC1)C2(CCCCC2)c3cc4ccccc4s3

InChI

1S/C19H25NS.ClH/c1-5-11-19(12-6-1,20-13-7-2-8-14-20)18-15-16-9-3-4-10-17(16)21-18;/h3-4,9-10,15H,1-2,5-8,11-14H2;1H

InChI key

XBOZTWUGBRZVBP-UHFFFAOYSA-N

Gene Information

human ... SLC6A3(6531)

Biochem/physiol Actions

BTCP is a potent and selective blocker of dopamine transport with little affinity for phencyclidine sites.

Features and Benefits

This compound is featured on the Biogenic Amine Transporters page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class Code

6.1B - Non-combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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X S He et al.
Journal of medicinal chemistry, 36(9), 1188-1193 (1993-04-30)
Piperidine and cyclohexyl ring homologues of the high-affinity dopamine (DA) uptake inhibitor 1-[1-(2-benzo[b]thienyl)cyclohexyl]piperidine (BTCP, 3) were each prepared in four steps from the appropriate cycloalkanones. These compounds were tested for their ability to displace [3H]BTCP and [3H]cocaine and to inhibit
T Maurice et al.
General pharmacology, 24(1), 191-194 (1993-01-01)
1. [3H]N-[1-(2-Benzo(b)thiophenyl)cyclohexyl]piperidine ([3H]BTCP) labels in vivo the dopamine uptake complex in the mouse striatum. 2. In mice treated with gamma-butyrolactone (GBL, 400 mg/kg), [3H]BTCP specific binding was increased and ID50 values of BTCP and cocaine for the prevention of [3H]BTCP
C Deleuze-Masquefa et al.
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, 9(4), 345-354 (2000-02-09)
1-[1-(2-Benzo[b]thiopheneyl)cyclohexyl]piperidine hydrochloride (BTCP) and cocaine bind to the neuronal dopamine transporter (DAT) to strongly inhibit dopamine (DA) reuptake. Although similar to acute administration, cocaine and BTCP produce sensitization and tolerance, respectively, on chronic administration. We previously found that liver microsomes
W Koek et al.
The Journal of pharmacology and experimental therapeutics, 250(3), 1019-1027 (1989-09-01)
Phencyclidine (PCP) inhibits dopamine (DA) uptake and acts as a noncompetitive N-methyl-D-aspartate antagonist by binding to PCP receptors. The PCP analog N-[1-(2-benzo(b)thiophenyl) cyclohexyl]piperidine (BTCP, GK13) is a potent DA uptake inhibitor, but has low affinity for PCP receptors. The behavioral
G Attali et al.
Brain research, 756(1-2), 153-159 (1997-05-09)
The present study was designed to investigate the modulatory effect of gonadal steroids on brain dopamine (DA) and serotonin (5-HT) presynaptic transporters in female and male rats. Female and male rats were castrated and treated with either vehicle or gonadal
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