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SML1882

Sigma-Aldrich

RS 67333 hydrochloride

≥98% (HPLC)

Synonym(s):

1-(4-Amino-5-chloro-2-methoxy-phenyl)-3-[1(n-butyl)-4-piperidinyl]-1-propanone hydrochloride, 1-(4-Amino-5-chloro-2-methoxyphenyl)-3-(1-butyl-4-piperidinyl)-1-propanone hydrochloride, RS-67,333 hydrochloride, RS-67333 hydrochloride, RS67333 hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C19H29ClN2O2 ·HCl
CAS Number:
168986-60-5
Molecular Weight:
389.36
MDL number:
MFCD00938576
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

H2O: 1 mg/mL, clear (warmed)

storage temp.

room temp

SMILES string

O=C(C1=CC(Cl)=C(N)C=C1OC)CCC2CCN(CCCC)CC2.[H]Cl

InChI

1S/C19H29ClN2O2.ClH/c1-3-4-9-22-10-7-14(8-11-22)5-6-18(23)15-12-16(20)17(21)13-19(15)24-2;/h12-14H,3-11,21H2,1-2H3;1H

InChI key

XVBGLZNYWUUAFF-UHFFFAOYSA-N

Biochem/physiol Actions

A selective and potent 5-HT4 partial agonist with in vitro and in vivo efficacy.
RS 67333 is a selective, high affinity (pKi = 8.7 for the 5-HT4 binding site in guinea-pig striatum) partial agonist toward 5-HT4 receptor that relaxes carbachol-contracted rat oesphageal muscularis mucosae ex vivo (pEC50/%reversal = 8.7/50 with RS 67333 vs. 8.2/100 with 5-HT) and induces tachycardia (tachyarrhythmia) of anaesthetized micropigs in vivo (ED50 via i.p. in μg/kg over max heart rate increase in beats/min = 4.9/35 with RS 67333 vs. 3.2/95 with 5-HT). RS 67333 is also reported to show high affinity for sigma receptors (pKi = 8.9/σ1 and 8.0/σ2), while exhibiting much reduced affinity toward a panel of other receptors, including 5-HT1A, 5-HT2A, 5-HT2C, 5-HT3 (pKi <6.4), muscarinic receptors (pKi = 5.2/M1 & 5.3/M2), and adrenoceptors (pKi <6.7 for α1A, α1B, α2A, α2B, β1, β2).

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000011932
0000011931
057M4705V

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E Marchetti et al.
Neuropharmacology, 39(11), 2017-2027 (2000-08-30)
Recent data suggest that activation of 5-HT(4) receptors may modulate cognitive processes such as learning and memory. In the present study, the effects of two potent and selective 5-HT(4) agonists, RS 17017 [1-(4-amino-5-chloro-2-methoxyphenyl)-5- (piperidin-1-yl)-1-pentanone hydrochloride] and RS 67333 [1(4-amino-5-chloro-2-methoxyphenyl)-3- (1-n-butyl-4-piperidinyl)-1-propanone]
Mohammad Nasehi et al.
Behavioural brain research, 317, 272-278 (2016-10-28)
Functional interaction between cannabinoid and serotonin neuronal systems have been reported in different tasks related to memory assessment. The present study investigated the effect of serotonin 5-HT4 agents into the dorsal hippocampus (the CA1 region) on spatial and object novelty
R M Eglen et al.
British journal of pharmacology, 115(8), 1387-1392 (1995-08-01)
1. The pharmacology of two novel 5-HT4 receptor agonists, RS 67333 (1-(4-amino-5-chloro-2-methoxy-phenyl)-3-[1(n-butyl)-4-piperidinyl]-1- propanone HCl) and RS 67506 (1-(4-amino-5-chloro-2-methoxy-phenyl)-3-[1-(2-methyl sulphonylamino)ethyl-4-piperidinyl]-1-propanone HCl) have been assessed in vitro and in vivo. 2. RS 67333 and RS 67506 exhibited affinities (pKi = 8.7 and

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