2-Diphenylmethylpyrrolidine

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2-Diphenylmethylpyrrolidine
2-Diphenylmethylpyrrolidine.png
Legal status
Legal status
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class B
Identifiers
  • 2-(Diphenylmethyl)pyrrolidine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard 100.162.251 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C17H19N
Molar mass 237.339 g·mol−1
3D model (JSmol)
  • c1cc(ccc1)C(c2ccccc2)C3NCCC3
  • InChI=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 Yes check.svgY
  • Key:OXOBKZZXZVFOBB-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

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. [1] [2] [3] Literature data suggest that it can produce the same psychotropic effects as other stimulants, but with a longer duration of action. [4]

Desoxy-D2PM has two enantiomers which are used industrially in their purified form as chiral derivatizing agents during chemical synthesis. [5]

As of 4 November 2010, the UK Home Office announced a ban on the importation of 2-diphenylmethylpyrrolidine, following a recommendation from the ACMD. [6] It was due to become a class B drug [7] on 28 March 2012, [8] but the bill was scrapped, due to the presence of two steroids included in the bill that were later recommended to remain uncontrolled. [9]

It was made a class B drug and placed in Schedule I on 13 June 2012. [10]

Related Research Articles

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The Misuse of Drugs Act 1971 is an Act of the Parliament of the United Kingdom. It represents action in line with treaty commitments under the Single Convention on Narcotic Drugs, the Convention on Psychotropic Substances, and the United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances.

<span class="mw-page-title-main">PRO-LAD</span> Chemical compound

PRO-LAD is an analogue of LSD. It is described by Alexander Shulgin in the book TiHKAL. PRO-LAD is a psychedelic drug similar to LSD, and is around as potent as LSD itself with an active dose reported at between 100 and 200 micrograms.

<span class="mw-page-title-main">Phenazepam</span> Chemical compound

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<span class="mw-page-title-main">Methylenedioxypyrovalerone</span> Chemical compound

Methylenedioxypyrovalerone (MDPV) is a stimulant of the cathinone class that acts as a norepinephrine–dopamine reuptake inhibitor (NDRI). It was first developed in the 1960s by a team at Boehringer Ingelheim. Its activity at the dopamine transporter is six times stronger than at the norepinephrine transporter and it is virtually inactive at the serotonin transporter. MDPV remained an obscure stimulant until around 2004 when it was reportedly sold as a designer drug. In the US, products containing MDPV and labeled as bath salts were sold as recreational drugs in gas stations, similar to the marketing for Spice and K2 as incense, until it was banned in 2011.

<span class="mw-page-title-main">Desoxypipradrol</span> Chemical compound

Desoxypipradrol, also known as 2-⁠diphenylmethylpiperidine (2-DPMP), is a drug developed by Ciba in the 1950s which acts as a norepinephrine-dopamine reuptake inhibitor (NDRI).

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<span class="mw-page-title-main">Lysergic acid 2,4-dimethylazetidide</span> Chemical compound

Lysergic acid 2,4-dimethylazetidide (LA-SS-Az, LSZ) is an analog of LSD developed by the team led by David E. Nichols at Purdue University. It was developed as a rigid analog of LSD with the diethylamide group constrained into an azetidine ring in order to map the binding site at the 5-HT2A receptor. There are three possible stereoisomers around the azetidine ring, with the (S,S)-(+) isomer being the most active, slightly more potent than LSD itself in drug discrimination tests using trained rats.

<span class="mw-page-title-main">5-IT</span> Chemical compound

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<span class="mw-page-title-main">Substituted cathinone</span> Class of chemical compounds

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<span class="mw-page-title-main">Methoxetamine</span> Dissociative drug

Methoxetamine, abbreviated as MXE, is a dissociative hallucinogen that has been sold as a designer drug. It differs from many dissociatives such as ketamine and phencyclidine (PCP) that were developed as pharmaceutical drugs for use as general anesthetics in that it was designed specifically to increase the antidepressant effects of ketamine.

<span class="mw-page-title-main">Methiopropamine</span> Structural analog of methamphetamine

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<span class="mw-page-title-main">3-Methylmethcathinone</span> Substituted cathinone designer drug

3-Methylmethcathinone, also known as 3-MMC and metaphedrone, is a designer drug from the substituted cathinone family. 3-MMC is closely related in structure to the more commonly known illicit drug mephedrone (4-MMC), and is also illegal in most countries that have banned mephedrone due to 3-MMC being a structural isomer of 4-MMC. However, 3-MMC has still appeared on the recreational drug market as an alternative to mephedrone, and was first identified being sold in Sweden in 2012. Unlike some synthetic cathinones, 3-MMC has been evaluated in at least one large mammal study. 3-MMC is a monoamine transporter substrate that potently inhibits norepinephrine uptake and displays more pronounced dopaminergic vs. serotonergic activity.

References

  1. De Paoli G, Brandt SD, Pounder DJ (December 2011). "Analytical characterization and rapid determination of 2-(diphenylmethyl)pyrrolidine in blood and application to an internet product". Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences. 879 (31): 3771–4. doi:10.1016/j.jchromb.2011.10.014. PMID   22055832.
  2. "2-(Diphenylmethyl)pyrrolidine (desoxy-D2PM)" (in Italian). Dipartimento Politiche Antidroga, Rome. Archived from the original (pdf) on 27 February 2013. Retrieved 10 February 2012.
  3. DC Shanie Nayar. "Green Powder called A3A Methano" (PDF). Archived from the original (PDF) on 27 February 2013. Retrieved 10 February 2012.
  4. Coppola M, Mondola R (July 2012). "Research chemicals marketed as legal highs: the case of pipradrol derivatives". Toxicology Letters. 212 (1): 57–60. doi:10.1016/j.toxlet.2012.04.019. PMID   22564760.
  5. Bertelsen S, Halland N, Bachmann S, Marigo M, Braunton A, Jørgensen KA (October 2005). "Organocatalytic asymmetric alpha-bromination of aldehydes and ketones". Chemical Communications (38): 4821–3. doi:10.1039/b509366j. PMID   16193126.
  6. Import ban on psychoactive drug Archived 29 August 2012 at the Wayback Machine , UK Home Office
  7. "The Misuse of Drugs Act 1971 (Amendment) Order 2012" (PDF). UK Home Office. 27 January 2012. Archived from the original on 1 January 2013. Retrieved 11 March 2012.
  8. "Government accepts ACMD's advice to schedule D2PM, 2-DPMP and phenzepam" (PDF). UK Home Office. 27 January 2012. Archived from the original on 6 April 2012. Retrieved 11 March 2012.
  9. "ACMD letter on further advice on the classification of two steroidal substances - February 2012" (PDF). UK Home Office. 14 February 2012. Archived from the original on 5 April 2012. Retrieved 18 March 2012.
  10. "A Change to the Misuse of Drugs Act 1971: control of pipradrol-related compounds and phenazepam". UK Home Office. 7 June 2012. Archived from the original on 30 October 2012. Retrieved 30 July 2012.