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Diphenidine: Difference between revisions
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'''Diphenidine''' (also known as DPD, DND, 1,2-DEP, and DPH) is a lesser-known novel [[psychoactive class::dissociative]] substance of the [[chemical class::diarylethylamine]] class. It is structurally similar to [[methoxphenidine]] (MXP) and [[ephenidine]]. It is classified as an [[NMDA receptor antagonist]].<ref name="wallach">Wallach, J., Kang, H., Colestock, T., Morris, H., Bortolotto, Z. A., Collingridge, G. L., ... | '''Diphenidine''' (also known as DPD, DND, 1,2-DEP, and DPH) is a lesser-known novel [[psychoactive class::dissociative]] substance of the [[chemical class::diarylethylamine]] class. It is structurally similar to [[methoxphenidine]] (MXP) and [[ephenidine]]. It is classified as an [[NMDA receptor antagonist]].<ref name="wallach">{{cite journal | vauthors=((Wallach, J.)), ((Kang, H.)), ((Colestock, T.)), ((Morris, H.)), ((Bortolotto, Z. A.)), ((Collingridge, G. L.)), ((Lodge, D.)), ((Halberstadt, A. L.)), ((Brandt, S. D.)), ((Adejare, A.)) | veditors=((Lee, J.)) | journal=PLOS ONE | title=Pharmacological Investigations of the Dissociative ‘Legal Highs’ Diphenidine, Methoxphenidine and Analogues | volume=11 | issue=6 | pages=e0157021 | date=17 June 2016 | url=https://dx.plos.org/10.1371/journal.pone.0157021 | issn=1932-6203 | doi=10.1371/journal.pone.0157021}}</ref> | ||
The synthesis of diphenidine was first reported in 1924. Shortly after the 2013 UK [[arylcyclohexylamine]] ban, diphenidine and the related compound [[methoxphenidine]] became available on the grey market. In 2014, there were two cases of diphenidine being sold in combination with synthetic cannabinoids in Japanese herbal incense blends, one of which was implicated in a fatal overdose. | The original synthesis of diphenidine was first reported in 1924.{{citation needed}} However, it was not selected for further development. Shortly after the 2013 UK [[arylcyclohexylamine]] ban, diphenidine and the related compound [[methoxphenidine]] became available on the grey market. In 2014, there were two cases of diphenidine being sold in combination with synthetic cannabinoids in Japanese herbal incense blends, one of which was implicated in a fatal overdose. | ||
[[Subjective effects]] include [[stimulation]], [[motor control loss]], [[pain relief]], [[internal hallucinations]], [[conceptual thinking]], [[euphoria]], and [[disconnective effects|dissociation]]. Dissociation is a complex mental state characterized by perceptual distortions and feelings of detachment from the environment and one's self. Anecdotal reports describe high doses of diphenidine producing "''bizarre somatosensory phenomena and transient anterograde amnesia''."<ref>From PCP to MXE: a comprehensive review of the non-medical use of dissociative drugs | | [[Subjective effects]] include [[stimulation]], [[motor control loss]], [[pain relief]], [[internal hallucinations]], [[conceptual thinking]], [[euphoria]], and [[disconnective effects|dissociation]]. Dissociation is a complex mental state characterized by perceptual distortions and feelings of detachment from the environment and one's self. Anecdotal reports describe high doses of diphenidine producing "''bizarre somatosensory phenomena and transient anterograde amnesia''."<ref>{{cite journal | vauthors=((Morris, H.)), ((Wallach, J.)) | journal=Drug Testing and Analysis | title=From PCP to MXE: a comprehensive review of the non-medical use of dissociative drugs: PCP to MXE | volume=6 | issue=7–8 | pages=614–632 | date= July 2014 | url=https://onlinelibrary.wiley.com/doi/10.1002/dta.1620 | issn=19427603 | doi=10.1002/dta.1620}}</ref> The effects of diarylethylamines share similarities with [[arylcyclohexylamines]] like [[ketamine]] and [[phencyclidine]] ('''PCP'''), as well as [[dextromethorphan]] ('''DXM'''). | ||
Very little data exists about the pharmacological properties, metabolism, and toxicity of diphenidine in humans, and it has an extremely limited history of human usage. | Very little data exists about the pharmacological properties, metabolism, and toxicity of diphenidine in humans, and it has an extremely limited history of human usage. Some reports suggest that it may pose different toxicity risks than traditional dissociatives. It is also likely to have moderate to high abuse potential. As a result, it is highly advised to use [[harm reduction practices]] if using this substance. | ||
==History and culture== | ==History and culture== | ||
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The synthesis of diphenidine was first reported in 1924. It employed a nitrile displacement reaction analogous to the one that would later be used to discover [[phencyclidine]] in 1956. Shortly after the 2013 UK ban on [[arylcyclohexylamines]], diphenidine and the related compound [[methoxphenidine]] became available on the grey market. | The synthesis of diphenidine was first reported in 1924. It employed a nitrile displacement reaction analogous to the one that would later be used to discover [[phencyclidine]] in 1956. Shortly after the 2013 UK ban on [[arylcyclohexylamines]], diphenidine and the related compound [[methoxphenidine]] became available on the grey market. | ||
In 2014, there were two cases of diphenidine being sold in combination with synthetic [[cannabinoids]] in Japanese herbal incense blends. One herbal incense blend was found to contain diphenidine and [[5-fluoro-AB-PINACA]] at concentrations of 289 mg/g and 55.5 mg/g, respectively.<ref> | In 2014, there were two cases of diphenidine being sold in combination with synthetic [[cannabinoids]] in Japanese herbal incense blends. One herbal incense blend was found to contain diphenidine and [[5-fluoro-AB-PINACA]] at concentrations of 289 mg/g and 55.5 mg/g, respectively.<ref>{{cite journal | vauthors=((Wurita, A.)), ((Hasegawa, K.)), ((Minakata, K.)), ((Watanabe, K.)), ((Suzuki, O.)) | journal=Forensic Toxicology | title=A large amount of new designer drug diphenidine coexisting with a synthetic cannabinoid 5-fluoro-AB-PINACA found in a dubious herbal product | volume=32 | issue=2 | pages=331–337 | date=1 August 2014 | url=https://doi.org/10.1007/s11419-014-0240-y | issn=1860-8973 | doi=10.1007/s11419-014-0240-y}}</ref> Another product containing AB-CHMINACA, 5F-AMB, and diphenidine was implicated in a fatal overdose.<ref>{{cite journal | vauthors=((Hasegawa, K.)), ((Wurita, A.)), ((Minakata, K.)), ((Gonmori, K.)), ((Nozawa, H.)), ((Yamagishi, I.)), ((Watanabe, K.)), ((Suzuki, O.)) | journal=Forensic Toxicology | title=Postmortem distribution of AB-CHMINACA, 5-fluoro-AMB, and diphenidine in body fluids and solid tissues in a fatal poisoning case: usefulness of adipose tissue for detection of the drugs in unchanged forms | volume=33 | issue=1 | pages=45–53 | date=1 January 2015 | url=https://doi.org/10.1007/s11419-014-0245-6 | issn=1860-8973 | doi=10.1007/s11419-014-0245-6}}</ref> | ||
===Names=== | ===Names=== | ||
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==Chemistry== | ==Chemistry== | ||
[[File:80px-Piperidin.svg.png|thumb|80px|right|Generic structure of a piperdine molecule.]] | [[File:80px-Piperidin.svg.png|thumb|80px|right|Generic structure of a piperdine molecule.]] | ||
Diphenidine is a molecule of the diarylethylamine class. | Diphenidine is a molecule of the diarylethylamine class. The basic skeleton of diphenidine is a phenethylamine with a substituted Rα in phenyl ring. At the terminals of the piperidine ring, an amino group is attached through phenethylamine chain. Hence, diphenidine belongs to the piperidine dissociative class of compounds. Diphenidine is structurally analogous to [[MXP]], lacking a 2-methoxy substitution on one of its phenyl rings. | ||
==Pharmacology== | ==Pharmacology== | ||
{{Further|NMDA receptor antagonist}} | {{Further|NMDA receptor antagonist}} | ||
Diphenidine acts as an [[NMDA receptor antagonist]].<ref>NMDA receptor affinities of 1,2-diphenylethylamine and 1-(1,2-diphenylethyl)piperidine enantiomers and of related compounds | Diphenidine acts as an [[NMDA receptor antagonist]].<ref>{{cite journal | vauthors=((Berger, M. L.)), ((Schweifer, A.)), ((Rebernik, P.)), ((Hammerschmidt, F.)) | journal=Bioorganic & Medicinal Chemistry | title=NMDA receptor affinities of 1,2-diphenylethylamine and 1-(1,2-diphenylethyl)piperidine enantiomers and of related compounds | volume=17 | issue=9 | pages=3456–3462 | date=1 May 2009 | url=https://www.sciencedirect.com/science/article/pii/S0968089609002624 | issn=0968-0896 | doi=10.1016/j.bmc.2009.03.025}}</ref><ref>{{cite journal | vauthors=((Wallach, J.)), ((Kavanagh, P. V.)), ((McLaughlin, G.)), ((Morris, N.)), ((Power, J. D.)), ((Elliott, S. P.)), ((Mercier, M. S.)), ((Lodge, D.)), ((Morris, H.)), ((Dempster, N. M.)), ((Brandt, S. D.)) | journal=Drug Testing and Analysis | title=Preparation and characterization of the ‘research chemical’ diphenidine, its pyrrolidine analogue, and their 2,2-diphenylethyl isomers: Characterization of diphenylethylamines | volume=7 | issue=5 | pages=358–367 | date= May 2015 | url=https://onlinelibrary.wiley.com/doi/10.1002/dta.1689 | issn=19427603 | doi=10.1002/dta.1689}}</ref> NMDA receptors allow for electrical signals to pass between neurons in the brain and spinal column; for the signals to pass, the receptor must be open. Dissociatives close the NMDA receptors by blocking them. This disconnection of neurons leads to loss of feeling, difficulty moving, and eventually the famous “[[Visual_disconnection#Holes.2C_spaces_and_voids|hole]]”. | ||
Although vendors of diphenidine have stated the compound acts as a [[dopamine]]-[[Reuptake Inhibitor|reuptake inhibitor]] and a [[serotonin]] [[reuptake inhibitor]] with [[Opioid receptors|µ-opioid]] affinity and typical [[Dissociatives#Subjective effects|dissociative]] effects, to date diphenidine has not been screened for affinity at the dopamine transporter. If this is indeed the case, however, it provides an explanation for its euphoric and often stimulating effects. | Although vendors of diphenidine have stated the compound acts as a [[dopamine]]-[[Reuptake Inhibitor|reuptake inhibitor]] and a [[serotonin]] [[reuptake inhibitor]] with [[Opioid receptors|µ-opioid]] affinity and typical [[Dissociatives#Subjective effects|dissociative]] effects, to date diphenidine has not been screened for affinity at the dopamine transporter. If this is indeed the case, however, it provides an explanation for its euphoric and often stimulating effects. | ||
Diphenidine and related [[diarylethylamines]] have been studied in vitro as treatments for neurotoxic injury.<ref>1,2-diarylethylamines for treatment of neurotoxic injury | | Diphenidine and related [[diarylethylamines]] have been studied in vitro as treatments for neurotoxic injury.<ref>{{Citation | vauthors=((Gray, N. M.)), ((Cheng, B. K.)) | title=1,2-diarylethylamines for treatment of neurotoxic injury | url=https://worldwide.espacenet.com/publicationDetails/biblio?CC=EP&NR=0346791&KC=&FT=E&locale=en_EP}}</ref> Diphenidine may be a stronger NMDA receptor antagonist for neurogenesis, neurological repair and neuroprotection than other more common NMDA receptor antagonistic dissociatives such as [[ketamine]], [[dextromethorphan]], [[PCP]] analogs, [[Iboga]] and [[methoxetamine]]. | ||
==Subjective effects== | ==Subjective effects== | ||
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*'''[[Effect::Dizziness]]''' - Although uncommon, some people report dizziness under the influence of diphenidine. | *'''[[Effect::Dizziness]]''' - Although uncommon, some people report dizziness under the influence of diphenidine. | ||
*'''[[Effect::Nausea]]''' - It's worth noting that high dose diphenidine trips can sometimes result in nausea and vomiting at the peak of the trip. For most people, this is surprisingly not as unpleasant as they would initially expect due to the accompanying detachment from the physical senses. | *'''[[Effect::Nausea]]''' - It's worth noting that high dose diphenidine trips can sometimes result in nausea and vomiting at the peak of the trip. For most people, this is surprisingly not as unpleasant as they would initially expect due to the accompanying detachment from the physical senses. | ||
*'''[[Effect::Orgasm suppression]]''' - Orgasm enhancement can also be present, even at higher doses | *'''[[Effect::Orgasm suppression]]''' & '''[[Effect::Orgasm enhancement]]''' - Orgasm enhancement can sometimes also be present, even at higher doses, although this effect is not reliable. | ||
}} | }} | ||
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{{#ask: [[Category:Diphenidine]][[Category:Experience]]|format=ul|Columns=1}} | {{#ask: [[Category:Diphenidine]][[Category:Experience]]|format=ul|Columns=1}} | ||
Additional experience reports can be found here: | Additional experience reports can be found here: | ||
* [https://erowid.org/experiences/subs/exp_Diphenidine.shtml Erowid Experience Vaults: Diphenidine] | |||
*[https://erowid.org/experiences/subs/exp_Diphenidine.shtml Erowid Experience Vaults: Diphenidine] | |||
==Toxicity and harm potential== | ==Toxicity and harm potential== | ||
{{toxicity}} | |||
{{further|Research chemicals#Toxicity and harm potential|Responsible use #Hallucinogens}} | {{further|Research chemicals#Toxicity and harm potential|Responsible use #Hallucinogens}} | ||
The toxicity and long-term health effects of recreational diphenidine use do not | The toxicity and long-term health effects of recreational diphenidine use do not appear to have been studied in any scientific context and the [[Toxicity::exact toxic dosage is unknown]]. This is because diphenidine has very little history of human usage. | ||
Some anecdotal reports suggest diphenidine may increase the risk of [[mania]] and [[psychosis]]. This is common with many dissociatives, particularly with those that provide stimulation such as [[PCP]]. | |||
It has been reported that regular use can lead to increased blood pressure and rapid heart rate. | |||
It is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this substance. | It is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this substance. | ||
=== | ===Dependence and abuse potential=== | ||
As with other NMDA receptor antagonists, the chronic use of diphenidine can be considered [[Addiction potential::moderately addictive with a high potential for abuse]] | As with other NMDA receptor antagonists, the chronic use of diphenidine can be considered [[Addiction potential::moderately addictive with a high potential for abuse]]. It is likely capable of causing psychological dependence among certain users. When addiction has developed, cravings and [[withdrawal effects]] may occur if one suddenly stops their usage. | ||
Tolerance to many of the effects of diphenidine [[Time to full tolerance::develops with prolonged and repeated use]]. This results in users having to administer increasingly large doses to achieve the same effects. After that, it takes about [[Time to half tolerance::3 - 7 days]] for the tolerance to be reduced to half and [[Time to zero tolerance::1 - 2 weeks]] to be back at baseline (in the absence of further consumption). Diphenidine presents cross-tolerance with [[Cross-tolerance::all [[dissociative]]s]], meaning that after the consumption of diphenidine all [[dissociative]]s will have a reduced effect. | Tolerance to many of the effects of diphenidine [[Time to full tolerance::develops with prolonged and repeated use]]. This results in users having to administer increasingly large doses to achieve the same effects. After that, it takes about [[Time to half tolerance::3 - 7 days]] for the tolerance to be reduced to half and [[Time to zero tolerance::1 - 2 weeks]] to be back at baseline (in the absence of further consumption). Diphenidine presents cross-tolerance with [[Cross-tolerance::all [[dissociative]]s]], meaning that after the consumption of diphenidine all [[dissociative]]s will have a reduced effect. | ||
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Diphenidine is currently a legal grey area drug worldwide and is easily accessible through the use of online [[research chemical]] vendors. However, this does not guarantee anyone to be immune from legal prosecution should they be found in possession of this substance as the legality is likely to vary from country to country. | Diphenidine is currently a legal grey area drug worldwide and is easily accessible through the use of online [[research chemical]] vendors. However, this does not guarantee anyone to be immune from legal prosecution should they be found in possession of this substance as the legality is likely to vary from country to country. | ||
*'''Canada:''' As of March 2016, MT-45 and its analogues, one of which being Diphenidine, are Schedule I controlled substances.<ref>Regulations Amending the Food and Drug Regulations (Parts G and J — Lefetamine, AH-7921, MT-45 and W-18) | | *'''Canada:''' As of March 2016, MT-45 and its analogues, one of which being Diphenidine, are Schedule I controlled substances.<ref>{{Citation | vauthors=((Government of Canada, P. W. and G. S. C.)) | year=2016 | title=Canada Gazette – Regulations Amending the Food and Drug Regulations (Parts G and J — Lefetamine, AH-7921, MT-45 and W-18) | url=https://gazette.gc.ca/rp-pr/p2/2016/2016-06-01/html/sor-dors106-eng.html}}</ref> Possession without legal authority can result in maximum 7 years imprisonment. Only those with a law enforcement agency, person with an exemption permit or institutions with Minister's authorization may possess the drug. | ||
*'''Switzerland:''' Diphenidine is a controlled substance specifically named under Verzeichnis E.<ref>{{cite web|url=https://www.admin.ch/opc/de/classified-compilation/20101220/index.html|title=Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien|publisher=Bundeskanzlei [Federal Chancellery of Switzerland]|access-date=January 1, 2020|language=de}}</ref> | *'''Switzerland:''' Diphenidine is a controlled substance specifically named under Verzeichnis E.<ref>{{cite web|url=https://www.admin.ch/opc/de/classified-compilation/20101220/index.html|title=Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien|publisher=Bundeskanzlei [Federal Chancellery of Switzerland]|access-date=January 1, 2020|language=de}}</ref> | ||
*'''Turkey:''' Diphenidine is a classed as drug and is illegal to possess, produce, supply, or import.<ref name="Bakanlar Kurulu Kararı - Karar Sayısı : 2016/9712">https://resmigazete.gov.tr/eskiler/2017/01/20170112-8.pdf</ref> | *'''Turkey:''' Diphenidine is a classed as drug and is illegal to possess, produce, supply, or import.<ref name="Bakanlar Kurulu Kararı - Karar Sayısı : 2016/9712">https://resmigazete.gov.tr/eskiler/2017/01/20170112-8.pdf</ref> | ||
*'''United Kingdom:''' It is illegal to produce, supply, or import this drug under the Psychoactive Substance Act, which came into effect on May 26th, 2016.<ref>Psychoactive Substances Act 2016 | *'''United Kingdom:''' It is illegal to produce, supply, or import this drug under the Psychoactive Substance Act, which came into effect on May 26th, 2016.<ref>{{Citation | title=Psychoactive Substances Act 2016 | url=https://www.legislation.gov.uk/ukpga/2016/2/contents/enacted}}</ref> | ||
*'''United States:''' Diphenidine is a schedule II substance and is illegal without a prescription.<ref>https://www.unodc.org/LSS/Substance/Details/7ee627dd-c3ed-42d2-b84f-81edef0d6466</ref> | |||
==See also== | ==See also== | ||
*[[Responsible use]] | *[[Responsible use]] | ||
*[[Dissociative]] | *[[Dissociative]] | ||
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==External links== | ==External links== | ||
*[https://en.wikipedia.org/wiki/Diphenidine Diphenidine (Wikipedia)] | *[https://en.wikipedia.org/wiki/Diphenidine Diphenidine (Wikipedia)] | ||
*[https://isomerdesign.com/PiHKAL/explore.php?id=639 Diphenidine (Isomer Design)] | *[https://isomerdesign.com/PiHKAL/explore.php?id=639 Diphenidine (Isomer Design)] | ||
===Community=== | ===Community=== | ||
*[http://www.bluelight.org/vb/threads/668291-The-Big-amp-Dandy-Diphenidine-Thread The Big & Dandy Diphenidine Thread (Bluelight)] | *[http://www.bluelight.org/vb/threads/668291-The-Big-amp-Dandy-Diphenidine-Thread The Big & Dandy Diphenidine Thread (Bluelight)] | ||
==Literature== | ==Literature== | ||
* Wallach, J., Kang, H., Colestock, T., Morris, H., Bortolotto, Z. A., Collingridge, G. L., ... & Adejare, A. (2016). Pharmacological investigations of the dissociative ‘legal highs’ diphenidine, methoxphenidine and analogues. PLoS One, 11(6), e0157021. https://doi.org/10.1371/journal.pone.0157021 | |||
* Morris, H., & Wallach, J. (2014). From PCP to MXE: A comprehensive review of the non-medical use of dissociative drugs. Drug Testing and Analysis, 6(7–8), 614–632. https://doi.org/10.1002/dta.1620 | *Wallach, J., Kang, H., Colestock, T., Morris, H., Bortolotto, Z. A., Collingridge, G. L., ... & Adejare, A. (2016). Pharmacological investigations of the dissociative ‘legal highs’ diphenidine, methoxphenidine and analogues. PLoS One, 11(6), e0157021. https://doi.org/10.1371/journal.pone.0157021 | ||
*Morris, H., & Wallach, J. (2014). From PCP to MXE: A comprehensive review of the non-medical use of dissociative drugs. Drug Testing and Analysis, 6(7–8), 614–632. https://doi.org/10.1002/dta.1620 | |||
==References== | ==References== | ||
<references/> | <references /> | ||
{{#set:Featured=true}} | {{#set:Featured=true}} | ||