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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 blocker of dopamine transport.
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

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
098H4706V

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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
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
Charles Hainley et al.
Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine, 67(6), 1071-1073 (2009-03-07)
Methods are described to synthesize and characterize tritium labelled TCP and BTCP at high specific activity.
X He et al.
Journal of medicinal chemistry, 36(25), 4075-4081 (1993-12-10)
We previously reported (J. Med. Chem. 1993, 36, 1188-1193) that changes to the ring size of the piperidine and cyclohexyl rings of the high-affinity and selective dopamine (DA)-uptake inhibitor 1-[1-(2-benzo[b]thienyl)cyclohexyl]piperidine (BTCP, 2) caused different, and in some cases opposite, changes
F Espaze et al.
European journal of medicinal chemistry, 35(3), 323-331 (2000-04-29)
Congeners of the potent dopamine (DA) re-uptake inhibitor 1-[1-(2-benzo[b]thiophenyl)cyclohexyl]piperidine (BTCP) are unexpectedly able to bind in the rat cerebellum, although this structure is devoid of dopaminergic nerve endings. In line with previous studies the hypothesis that they bind to low
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