2-Diphenylmethylpyrrolidine

{{Short description|Stimulant designer drug}}

{{Use dmy dates|date=January 2015}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477213213

| IUPAC_name = 2-(Diphenylmethyl)pyrrolidine

| image = 2-Diphenylmethylpyrrolidine.png

| image_class = skin-invert-image

| width = 200

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| legal_DE = NpSG

| legal_UK = Class B

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| CAS_number = 119237-64-8

| CAS_number_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = UH7U0MAY6C

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| PubChem = 1295

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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 1256

| C=17 | H=19 | N=1

| smiles = c1cc(ccc1)C(c2ccccc2)C3NCCC3

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C17H19N/c1-3-8-14(9-4-1)17(16-12-7-13-18-16)15-10-5-2-6-11-15/h1-6,8-11,16-18H,7,12-13H2

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = OXOBKZZXZVFOBB-UHFFFAOYSA-N

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2-Diphenylmethylpyrrolidine (Desoxy-D2PM), also known as 2-benzhydrylpyrrolidine, is a stimulant psychoactive drug. It is the 4-dehydroxylated structural analog of diphenylprolinol (D2PM), and is also similar in structure to desoxypipradrol (2-DPMP), both of which act as norepinephrine-dopamine reuptake inhibitors (NDRIs). Like D2PM and 2-DPMP, Desoxy-D2PM is sold as a designer drug and has been used in the manufacture of legal highs. It has been marketed under the names A3A New Generation, A3A Methano, and Green Powder, and has been reported to cause hallucinations, violent behavior, dilated pupils, tachycardia, and high blood pressure.{{cite journal | vauthors = De Paoli G, Brandt SD, Pounder DJ | title = Analytical characterization and rapid determination of 2-(diphenylmethyl)pyrrolidine in blood and application to an internet product | journal = Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences | volume = 879 | issue = 31 | pages = 3771–4 | date = December 2011 | pmid = 22055832 | doi = 10.1016/j.jchromb.2011.10.014 }}{{Cite web|url=http://www.droganews.it/pubdownload.php?id=2472|title=2-(Diphenylmethyl)pyrrolidine (desoxy-D2PM)|format=pdf|publisher=Dipartimento Politiche Antidroga, Rome|language=IT|access-date=10 February 2012|archive-url=https://web.archive.org/web/20130227212129/http://www.droganews.it/pubdownload.php?id=2472|archive-date=27 February 2013|url-status=dead|df=dmy-all}}{{cite web|url=http://ewsd.wiv-isp.be/Other%20information%20on%20new%20psychoactive%20substances/Desoxy-D2PM/Report_UK_Dec%202010_Green%20Powder%20called%20A3A%20Methano.pdf|title=Green Powder called A3A Methano|author=DC Shanie Nayar|access-date=10 February 2012|archive-url=https://web.archive.org/web/20130227212132/http://ewsd.wiv-isp.be/Other%20information%20on%20new%20psychoactive%20substances/Desoxy-D2PM/Report_UK_Dec%202010_Green%20Powder%20called%20A3A%20Methano.pdf|archive-date=27 February 2013|url-status=dead}} Literature data suggest that it can produce the same psychotropic effects as other stimulants, but with a longer duration of action.{{cite journal | vauthors = Coppola M, Mondola R | title = Research chemicals marketed as legal highs: the case of pipradrol derivatives | journal = Toxicology Letters | volume = 212 | issue = 1 | pages = 57–60 | date = July 2012 | pmid = 22564760 | doi = 10.1016/j.toxlet.2012.04.019 }}

Desoxy-D2PM has two enantiomers which are used industrially in their purified form as chiral derivatizing agents during chemical synthesis.{{cite journal | vauthors = Bertelsen S, Halland N, Bachmann S, Marigo M, Braunton A, Jørgensen KA | title = Organocatalytic asymmetric alpha-bromination of aldehydes and ketones | journal = Chemical Communications | issue = 38 | pages = 4821–3 | date = October 2005 | pmid = 16193126 | doi = 10.1039/b509366j }}

As of 4 November 2010, the UK Home Office announced a ban on the importation of 2-diphenylmethylpyrrolidine, following a recommendation from the ACMD.[http://www.homeoffice.gov.uk/media-centre/news/drug-import-ban Import ban on psychoactive drug] {{Webarchive|url=https://web.archive.org/web/20120829050643/http://www.homeoffice.gov.uk/media-centre/news/drug-import-ban |date=29 August 2012 }}, UK Home Office It was due to become a class B drug{{cite web | url = http://www.legislation.gov.uk/ukdsi/2012/9780111520857/memorandum/contents | title = The Misuse of Drugs Act 1971 (Amendment) Order 2012 | access-date = 2012-03-11 | date = 2012-01-27 | format = PDF | publisher = UK Home Office | archive-date = 1 January 2013 | archive-url = https://web.archive.org/web/20130101010927/http://www.legislation.gov.uk/ukdsi/2012/9780111520857/memorandum/contents | url-status = live }} on 28 March 2012,{{cite web | url = http://www.homeoffice.gov.uk/publications/alcohol-drugs/drugs/2-dpmp-compounds/D2PM?view=Binary | title = Government accepts ACMD's advice to schedule D2PM, 2-DPMP and phenzepam | access-date = 2012-03-11 | date = 2012-01-27 | format = PDF | publisher = UK Home Office | archive-date = 6 April 2012 | archive-url = https://web.archive.org/web/20120406094033/http://www.homeoffice.gov.uk/publications/alcohol-drugs/drugs/2-dpmp-compounds/D2PM?view=Binary | url-status = live }} but the bill was scrapped, due to the presence of two steroids included in the bill that were later recommended to remain uncontrolled.{{cite web | url = http://www.homeoffice.gov.uk/publications/agencies-public-bodies/acmd1/acmd-steroids-advice-2012?view=Standard&pubID=1007793 | title = ACMD letter on further advice on the classification of two steroidal substances - February 2012 | access-date = 2012-03-18 | date = 2012-02-14 | format = PDF | publisher = UK Home Office | archive-date = 5 April 2012 | archive-url = https://web.archive.org/web/20120405213251/http://www.homeoffice.gov.uk/publications/agencies-public-bodies/acmd1/acmd-steroids-advice-2012?view=Standard&pubID=1007793 | url-status = live }}

It was made a class B drug and placed in Schedule I on 13 June 2012.{{cite web | url = http://homeoffice.gov.uk/about-us/corporate-publications-strategy/home-office-circulars/circulars-2012/014-2012/ | title = A Change to the Misuse of Drugs Act 1971: control of pipradrol-related compounds and phenazepam | access-date = 2012-07-30 | date = 7 Jun 2012 | publisher = UK Home Office | archive-date = 30 October 2012 | archive-url = https://web.archive.org/web/20121030144153/http://www.homeoffice.gov.uk/about-us/corporate-publications-strategy/home-office-circulars/circulars-2012/014-2012/ | url-status = live }}