Deoxypipradrol

Structural formula
	( R ) -form (left) and ( S ) -form (right) ; 1: 1 mixture ( racemate )
General
Non-proprietary name	Deoxypipradrol
other names	( RS ) -2- (Diphenylmethyl) piperidine ( IUPAC ); (±) -2- (Diphenylmethyl) piperidine; 2-benzhydryl piperidine;
Molecular formula	C 18 H 21 N
External identifiers / databases
EC number	208-276-6
ECHA InfoCard	100.007.525
PubChem	160506
Wikidata	Q414480
Drug information
Drug class	Stimulants
properties
Molar mass	251.37 g · mol -1
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
Toxicological data	50 mg kg −1 ( LD 50 , mouse , oral ) ; 80 mg kg −1 ( LD 50 , rat , oral ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Desoxypipradrol ( 2-diphenylmethylpiperidin , 2-DPMP ) is a drug selected from the group of piperidine - derivatives , of the stimulants belongs.

History and use

Deoxypipradrol was developed and researched by the pharmaceutical company Ciba-Geigy (now Novartis ) in the 1950s. It should be used in the treatment of narcolepsy and attention deficit / hyperactivity disorder . Despite the high degree of effectiveness, the development was not pursued any further because an alternative was developed by the same company: methylphenidate . Methylphenidate was believed to be the superior agent for treating ADHD because it has a shorter duration of action and its pharmacokinetic properties are more predictable than those of deoxypipradrol. As a result, other areas of use for deoxypipradrol have been sought, for example researching a faster recovery of sensation after anesthesia .

It is believed that deoxypipradrol is contained in various over-the-counter drug mixtures - known as bath salts - as an active ingredient and as a substitute for illegal amphetamines .

Manufacturing

Deoxypipradrol is a derivative of pipradrol , from which it can be obtained by reduction. Another manufacturing process is based on the condensation of 2-bromopyridine with diphenylacetonitrile in the presence of sodium amide and subsequent catalytic hydrogenation of the pyridine ring .

Side effects

The side effects of deoxypipradrol are comparable to those of pipradrol or other stimulants. When given for therapeutic purposes, sleep disorders , tachycardia , anorexia , dry mouth , tremor , arterial hypertension , euphoria , depression and psychoses can occur. Another side effect found in rats given 130 and 260 µmol / kg over a period of 14 days is hyperglycaemia . The side effect is more pronounced in young rats than in older rats.

Legal position

Germany

In Germany, deoxypipradrol is subject to BtMG Annex II .

United Kingdom

In the United Kingdom , following several cases of poisoning, the import of deoxypipradrol was banned under the Open General Import License effective November 4, 2011 . The Advisory Council on the Misuse of Drugs (ACMD) recommended monitoring at the same time as inclusion in the Misuse of Drugs Act ( Annex B / class B ). 2-DPMP has been classified as a class B drug since March 28, 2012 and is therefore prohibited.

literature

G. Bellucci: (2-Diphenylmethyl-piperidine hydrochloride and the methyl ester of 2-chloro-2-phenyl-2- (2-piperidyl) -acetic acid), drugs with waking effect in anesthesia. In: Minerva Anestesiologica , 1955 Jun, 21 (6), pp. 125-128 (Italian).

Individual evidence

↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ ^a ^b ^c ^d Les Iversen: Desoxypipradrol (2-DPMP) advice. Advisory Council on the Misuse of Drugs, September 13, 2011, p. 6.
↑ Entry on Desoxypipradrol. In: Römpp Online . Georg Thieme Verlag, accessed on April 8, 2016.
^ KL Hintze, HY Aboul-Enein, LJ Fischer: Isomeric specificity of diphenylmethylpiperidine in the production of rat pancreatic islet cell toxicity . In: Toxicology , 1977 Apr, 7 (2), pp. 133-140, PMID 324024 .
^ AK Chatterjee, LJ Fischer: Age-related susceptibility to the insulin-depleting action of 4-diphenylmethylpiperidine in young rats . In: Life Sci. , 1988, 43 (2), pp. 151-159, PMID 3292868 .
↑ Lord Henley: Government accepts ACMD's advice to schedule D2PM, 2-DPMP and phenzepam . (PDF) UK Home Office , January 26, 2012.

[NV-1] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[homeoffice-2] Les Iversen: Desoxypipradrol (2-DPMP) advice. Advisory Council on the Misuse of Drugs, September 13, 2011, p. 6.

[3] Entry on Desoxypipradrol. In: Römpp Online . Georg Thieme Verlag, accessed on April 8, 2016.

[4] KL Hintze, HY Aboul-Enein, LJ Fischer: Isomeric specificity of diphenylmethylpiperidine in the production of rat pancreatic islet cell toxicity . In: Toxicology , 1977 Apr, 7 (2), pp. 133-140, PMID 324024 .

[5] AK Chatterjee, LJ Fischer: Age-related susceptibility to the insulin-depleting action of 4-diphenylmethylpiperidine in young rats . In: Life Sci. , 1988, 43 (2), pp. 151-159, PMID 3292868 .

[6] Lord Henley: Government accepts ACMD's advice to schedule D2PM, 2-DPMP and phenzepam . (PDF) UK Home Office , January 26, 2012.