Pipradrol

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Pipradrol
Pipradrol.svg
Systematic (IUPAC) name
α,α-Diphenyl-2-piperidinemethanol
Clinical data
Legal status Schedule IV (US) Class C (UK/NZ)
Identifiers
CAS number 46-76-07 N
ATC code N06BX15
PubChem CID 10083
ChemSpider 9681 YesY
UNII S6I030E0DA YesY
Chemical data
Formula C18H21NO 
Mol. mass 267.37
 N (what is this?)  (verify)

Pipradrol (Meratran) is a mild central nervous system stimulant (norepinephrine-dopamine reuptake inhibitor) that is no longer widely used in most countries due to concerns about its abuse potential, although this is less of a problem than with other stimulants that still are in current use such as methylphenidate. Pipradrol is still used in some European countries, and even rarely in the USA. Pipradrol was developed in the 1940s,[1] and found use initially for treating obesity.[2] It was subsequently used for the treatment of a variety of other conditions such as narcolepsy, ADHD, and most particularly for counteracting the symptoms of senile dementia, this being the only application for which it is still used medically. Pipradrol proved useful for these applications as its relatively mild stimulant effects gave it a good safety profile compared to stronger stimulants. It was also trialled as an adjutant treatment for depression and schizophrenia although it was never widely used for these purposes.

Pipradrol was made illegal in many countries in the late 1970s, at the same time as many other drugs which had a history of abuse. The relatively mild stimulant effects of pipradrol meant that it was scheduled under the less restrictive classes in most countries (i.e. Class C in United Kingdom and New Zealand) but was still considered of sufficient abuse potential to be made an illegal drug. It is now an obscure compound that is virtually unknown as an illicit drug of abuse, but is still used for some scientific research, often as a comparison drug for testing other stimulants against.

Dosage is between 0.5 and 4 milligrams per day, typically taken as a single dose in the morning as the long duration of effects of pipradrol (up to 12 hours) means insomnia can be a problem especially if it is used at higher doses or taken too late in the day.

Common side effects include insomnia, anorexia, tachycardia, anxiety. Rarer side effects include dry mouth, tremor, hypertension, euphoria, depression, and very rarely psychosis or convulsions.

Synthesis[edit]

Typically made from reaction of ethyl pipecolinate hydrochloride with phenyl magnesium bromide.[3]

The second formally way of making pipradrol, analogous to the preparation Azacyclonol, is make the organometallic from 2-bromopyridine, this is reacted with benzophenone, then the heteroaromatic pyridine ring system is saturated with hydrogen to corresponding piperidine.[1][4]

See also[edit]

References[edit]

  1. ^ a b Charles H Tilford, Harold W Werner; Wm S Merrell Co; U.S. Patent 2,624,739 (1953).
  2. ^ Gelvin EP, McGavack TH, Kenigsberg S. Alpha-(2-piperidyl) benzhydrol hydrochloride (pipradrol) as an adjunct in the dietary management of obesity. N Y State J Med. 1955 Aug 15;55(16):2336-8.
  3. ^ Rao, A. V. Rama; Gurjar, M. K.; Sharma, P. A.; Kaiwar, Vijay; (March 1, 1990). "Enantioselective reductions of ketones with oxazaborolidines derived from (R and (S-α-α-diphenyl-2-piperdine methanol". Tetrahedron Letters 31 (16): 2341–2344. doi:10.1016/0040-4039(90)80223-9. 
  4. ^ . doi:10.1021/ja01192a01 (inactive 2014-07-30).  Missing or empty |title= (help) edit