2-Diphenylmethylpyrrolidine

Last updated

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 237.346 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

<span class="mw-page-title-main">Khat</span> Psychoactive species of plant

Khat, also known as Bushman's tea, especially in South Africa, is a flowering plant native to eastern and southeastern Africa. It has a history of cultivation originating in the Harar area and subsequently introduced at different times to countries nearby in East Africa and Southern Arabia, most notably Yemen. Cultivated by farmers, its leaves are sold on the market to be chewed as a recreational stimulant. The world's largest consumers are Eastern Africans, particularly Somalis, and nearby Yemen, with the largest producers/exporters being Ethiopia and Kenya.

<span class="mw-page-title-main">Misuse of Drugs Act 1971</span> United Kingdom legislation

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> Benzodiazepine drug

Phenazepam is a benzodiazepine drug, first developed in the Soviet Union in 1975, and now produced in Russia and several other countries.

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

Methylenedioxypyrovalerone 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">Pipradrol</span> CNS stimulant medication

Pipradrol, also known by its brand name Meratran, is a mild central nervous system stimulant that acts as a norepinephrine-dopamine reuptake inhibitor. Developed in the United States in the 1940s and patented in 1953, pipradrol was initially marketed as an antidepressant in the mid-1950s. It was subsequently used as an adjunct treatment for various conditions, including obesity, senile dementia, narcolepsy, and schizophrenia.

<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).

<span class="mw-page-title-main">Mephedrone</span> Synthetic stimulant drug

Mephedrone, also known as 4-methylmethcathinone, 4-MMC, and 4-methylephedrone, is a synthetic stimulant drug belonging to the amphetamine and cathinone classes. It is commonly referred to by slang names such as drone, M-CAT, White Magic, meow meow, and bubble. Chemically, it is similar to the cathinone compounds found in the Khat plant, native to eastern Africa.

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

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<span class="mw-page-title-main">3-MeO-PCP</span> Chemical compound

3-Methoxyphencyclidine (3-MeO-PCP) is a dissociative hallucinogen of the arylcyclohexylamine class related to phencyclidine (PCP) which has been sold online as a designer drug. It has been used across Europe and the United States. In some cases, consumption has been known to be fatal. It acts mainly as an NMDA receptor antagonist, though it has also been found to interact with the sigma σ1 receptor and the serotonin transporter. The drug does not possess any opioid activity nor does it act as a dopamine reuptake inhibitor.

<span class="mw-page-title-main">4-MeO-PCP</span> Chemical compound

4-Methoxyphencyclidine is a dissociative anesthetic drug that has been sold online as a research chemical. The synthesis of 4-MeO-PCP was first reported in 1965 by the Parke-Davis medicinal chemist Victor Maddox. A 1999 review published by a chemist using the pseudonym John Q. Beagle suggested the potency of 4-MeO-PCP in man was reduced relative to PCP, two years later Beagle published a detailed description of the synthesis and qualitative effects of 4-MeO-PCP, which he said possessed 70% the potency of PCP. 4-MeO-PCP was the first arylcyclohexylamine research chemical to be sold online, it was introduced in late 2008 by a company trading under the name CBAY and was followed by several related compounds such as 3-MeO-PCP and methoxetamine. 4-MeO-PCP has lower affinity for the NMDA receptor than PCP, but higher affinity than ketamine, it is orally active in a dosage range similar to ketamine, with some users requiring doses in excess of 100 mg for desired effects. Users have reported substantial differences in active dose, these discrepancies can be partially explained by the presence of unreacted PCC and other impurities in samples sold on the grey market. 4-MeO-PCP has Ki values of 404 nM for the NMDA receptor, 713 nM for the norepinephrine transporter, 844 nM for the serotonin transporter, 296 nM for the σ1 receptor and 143 nM for the σ2 receptor.

<span class="mw-page-title-main">6-APB</span> Psychoactive drug

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

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Methiopropamine (MPA), also known as N-methylthiopropamine, is an organic compound structurally related to methamphetamine. Originally reported in 1942, the molecule consists of a thiophene group with an alkyl amine substituent at the 2-position. It appeared for public sale in the United Kingdom in December 2010 as a "research chemical" or "legal high", recently branded as Blow. It has limited popularity as a recreational stimulant.

A temporary class drug is a relatively new status for controlled drugs, which has been adopted in some jurisdictions, notably New Zealand and the United Kingdom, to attempt to bring newly synthesised designer drugs under legal control. The controlled drug legislation in these jurisdictions requires drug scheduling decisions to follow an evidence-based process, where the harms of the drug are assessed and reviewed so that an appropriate legal status can be assigned. Since many designer drugs sold in recent years have had little or no published research that could help inform such a decision, they have been widely sold as "legal highs", often for months, before sufficient evidence accumulates to justify placing them on the controlled drug schedules.

<span class="mw-page-title-main">Bath salts (drug)</span> Recreational drug often superficially resembling true bath salts

Bath salts are a group of recreational designer drugs. The name derives from instances in which the drugs were disguised as bath salts. The white powder, granules, or crystals often resemble Epsom salts, but differ chemically. The drugs' packaging often states "not for human consumption" in an attempt to circumvent drug prohibition laws. Additionally, they may be described as "plant food", "powdered cleaner", or other products.

<span class="mw-page-title-main">Diphenyl-2-pyridylmethane</span> Chemical compound

Diphenyl-2-pyridylmethane is a triaryl organic compound that has been used to selectively extract specific metal ions into organic solvents. Its pharmacology is similar to the stimulant desoxypipradrol in which the pyridine ring is reduced to a piperidine and for which it is a chemical precursor.

<span class="mw-page-title-main">4,4'-Dimethylaminorex</span> Chemical compound

4,4'-Dimethylaminorex, sometimes referred to by the street name "Serotoni", is a psychostimulant and entactogen designer drug related to aminorex, 4-methylaminorex, and pemoline. It was first detected in the Netherlands in December 2012, and has been sold as a designer drug around Europe since mid-2013.

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.