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Merck
CN

D007

R(−)-Chloroethylnorapomorphine hydrochloride

analytical standard

Synonym(s):

NCA hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C18H18ClNO2 · HCl
CAS Number:
75344-87-5
Molecular Weight:
352.25
NACRES:
NA.24
PubChem Substance ID:
329798579
UNSPSC Code:
41116107
MDL number:
MFCD00069237

Key Documents

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storage condition

protect from light, desiccated

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

InChI

1S/C18H18ClNO2.ClH/c19-7-9-20-8-6-11-2-1-3-13-16(11)14(20)10-12-4-5-15(21)18(22)17(12)13;/h1-5,14,21-22H,6-10H2;1H/t14-;/m1./s1

SMILES string

Cl.Oc1ccc2C[C@H]3N(CCCl)CCc4cccc(c34)-c2c1O

InChI key

ASPGECRWCJCPPO-PFEQFJNWSA-N

grade

analytical standard

assay

≥85%

form

solid

color

off-white

solubility

0.1 M HCl: soluble, H2O: soluble, aqueous base: unstable

format

neat

storage temp.

2-8°C

Quality Level

100

Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Biochem/physiol Actions

Irreversible dopamine receptor alkylating agent

Preparation Note

Dissolve in oxygen-free boiled water containing 0.1% sodium metabisulfite or other antioxidants. Solutions should be freshly prepared.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H336

Hazard Classifications

STOT SE 3

target_organs

Central nervous system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

涉药品监管产品
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Certificates of Analysis (COA)

Lot/Batch Number
FN04182017
FN02172220

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G J Kilpatrick et al.
European journal of pharmacology, 107(1), 71-78 (1984-12-15)
N-(chloroethyl)-norapomorphine (NCA) irreversibly inhibits striatal dopamine function, the binding of dopamine agonist ligands and dopamine-stimulated adenylate cyclase. A selective interaction of [3H]NCA with dopamine receptor sites would be of use in the characterisation and isolation of brain dopamine receptors. In
J Lehmann et al.
European journal of pharmacology, 90(4), 393-400 (1983-06-17)
(-)-N-(2-Chloroethyl)-norapomorphine [-)-NCA) inhibited in a concentration-dependent manner the electrically evoked [3H]acetylcholine release in slices of cat caudate. The inhibition by (-)-NCA was reversible and antagonized by the benzamide neuroleptic S-sulpiride. Although (-)-NCA is an irreversible antagonist at some behaviorally relevant
Dopamine autoreceptors differ pharmacologically from postsynaptic dopamine receptors: effects of (-)-N-(2-chloroethyl)-norapomorphine.
J Lehmann et al.
European journal of pharmacology, 77(1), 85-86 (1982-01-08)
S A Cohen et al.
Journal of medicinal chemistry, 26(10), 1348-1353 (1983-10-01)
The rates and mechanism of solvolysis of (-)-N-(2-chloroethyl)norapomorphine (NCA, 1c) in aqueous solution have been examined by reversed-phase liquid chromatography (HPLC) to follow the levels of starting material and products. The first-order rate constants for aziridinium ion formation at 25
J H Guan et al.
Journal of medicinal chemistry, 27(6), 806-810 (1984-06-01)
The synthesis of the title compounds (1c and its 2H isomer 1b) from N-(2-hydroxyethyl)norapomorphine was carried out by ring bromination, followed by chlorination to the 2-chloroethyl compound 6. Further reduction with 2H2 or 3H2 and Pd/C gave 1b or 1c.
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