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Prolintane (hydrochloride)

(Synonyms: NSC 169914; SP 732) 目录号 : GC44695

An Analytical Reference Material

Prolintane (hydrochloride) Chemical Structure

Cas No.:1211-28-5

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产品描述

Prolintane (hydrochloride) is an analytical reference material that is structurally classified as an amphetamine. It produces stimulant activity by inhibiting transporters for certain monoamine neurotransmitters, including dopamine and norepinephrine, preventing their uptake.[1] Reports of its abuse have been documented.[2] This product is intended for research and forensic applications.

Reference:
[1]. Nicholson, A.N., and Stone, B.M. Heterocyclic amphetamine derivatives and caffeine on sleep in man. Br. J. Clin. Pharmacol. 9(2), 195-203 (1980).
[2]. Kyle, P.B., and Daley, W.P. Domestic abuse of the European rave drug prolintane. J. Anal. Toxicol. 31(7), 415-418 (2007).

Chemical Properties

Cas No. 1211-28-5 SDF
别名 NSC 169914; SP 732
化学名 1-[1-(phenylmethyl)butyl]-pyrrolidine, monohydrochloride
Canonical SMILES CCCC(N1CCCC1)CC2=CC=CC=C2.Cl
分子式 C15H23N•HCl 分子量 253.8
溶解度 N/A 储存条件 Store at -20°C
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1 mM 3.9401 mL 19.7006 mL 39.4011 mL
5 mM 0.788 mL 3.9401 mL 7.8802 mL
10 mM 0.394 mL 1.9701 mL 3.9401 mL
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Research Update

The abuse potential of Prolintane in rodents: Behavioral pharmacology approaches

Neuropharmacology 2022 Mar 1;205:108917.PMID:34896117DOI:10.1016/j.neuropharm.2021.108917.

Prolintane (1-Phenyl-2-pyrrolidinylpentane), a synthetic central nervous system (CNS) stimulant, is structurally similar to amphetamine but pharmacologically acts as a dopamine reuptake inhibitor like cocaine. While several case studies reported adverse effects and recreational use of Prolintane, the abuse potential of the drug has not been systemically examined yet. In the present study, we evaluated the behavioral effects of Prolintane regarding its abuse liability in rodents using locomotor activity, conditioned place preference (CPP), self-administration (SA), and drug discrimination paradigms, as well as in-vivo microdialysis experiment. First, acute Prolintane (10 and 20 mg/kg, intraperitoneal injection) increased locomotor activity (distance traveled, cm) in mice but to a lesser degree than methamphetamine (as a positive control). We also found that a single and solitary injection of Prolintane (20 mg/kg, IP) significantly increased extracellular dopamine in the striatum. The following result suggests that its stimulatory effects might be associated with the mesolimbic dopaminergic pathway. Further, Prolintane produced a significant drug-paired place preference at doses of both 10 and 20 mg/kg. In the SA experiment, the mice that self-administered Prolintane intravenously (4 mg/kg/inf) showed a higher infusion and active lever responses but not inactive lever responses. Additionally, cumulative doses of Prolintane partially elicited cocaine-appropriate lever responses (38.57% at doses up to 10 mg/kg) in rats. These results implied that Prolintane has not only rewarding and reinforcing effects but also interoceptive stimulus properties, which are similar to cocaine at a moderate level. Taken together, this study was the first to show, to our knowledge, that Prolintane has a certain level of abuse potential and should be considered carefully as a valuable basis for legal restrictions on use.

Domestic abuse of the European rave drug Prolintane

J Anal Toxicol 2007 Sep;31(7):415-8.PMID:17725890DOI:10.1093/jat/31.7.415.

Prolintane is a sympathomimetic amine with pharmacologic properties similar to d-amphetamine. Side effects include insomnia, nervousness, and irritability. Overdoses of Prolintane may cause hallucinations, psychosis, and death. The drug is commonly prescribed in Africa, Australia, and Europe but is not available in the United States. This manuscript reports the first medically documented cases of Prolintane abuse in the United States. In the first, a 34-year-old male presented to the emergency department confused, agitated, and unable to follow commands. Initial drug and alcohol screens were negative, but analysis by gas chromatography-mass spectrometry (GC-MS) indicated the presence of amitriptyline, nortriptyline, nicotine, and Prolintane. The second patient, a healthy 26-year-old female, presented to the emergency department after intrauterine fetal death and spontaneous delivery. GC-MS revealed the presence of multiple drugs, including cannabinoids, cocaine, nicotine, hydrocodone, and Prolintane. The medical and scientific communities should be aware of the potential for Prolintane abuse because it may cause symptoms similar to those of the amphetamines but is not likely to be detected by a routine urine drug screen.

Study on the metabolism of racemic Prolintane and its optically pure enantiomers

Xenobiotica 1992 Feb;22(2):143-52.PMID:1632104DOI:10.3109/00498259209046613.

1. Asian and European volunteers were given racemic Prolintane, and the metabolites in the 24 h urine were identified and quantified by g.l.c. mass spectroscopy using synthetic reference compounds. 2. R-(+)- and S-(-)-prolintane were synthesized from optically active phenylalanine. The metabolism of the enantiomers differs mainly in the quantitative amounts of metabolites.

Effects of Prolintane on 3,4-dihydroxyphenylacetic acid concentration in rat brain after spiperone treatment

Pharmacol Biochem Behav 1979 Apr;10(4):561-3.PMID:572552DOI:10.1016/0091-3057(79)90233-8.

Prolintane (1-[alpha-propylphenethyl]-pyrrolidine) but not l-(alpha-methylphenethyl)-pyrrolidine markedly enhanced the increase in 3,4-dihydroxyphenylacetic acid concentration in the brains of rats treated with spiperone, a neuroleptic drug. This action and other properties of Prolintane described in the literature place it in a group of stimulant drugs that includes methylphenidate, cocaine and amfonelic acid with properties that differ from those of amphetamine.

[Synthesis of metabolites and enantiomers of Prolintane]

Arch Pharm (Weinheim) 1992 Jan;325(1):47-52.PMID:1605711DOI:10.1002/ardp.19923250111.

The synthesis of 15 possible metabolites of Prolintane (1) (Katovit) which is used in the treatment of blood pressure disregulations is described. Furthermore, the preparation of the enantiomers of 1 is reported, starting with R-(+)- and S-(-)-phenylalaninol respectively.