Diphenyl-2-pyridylmethane: Difference between revisions

From Wikipedia, the free encyclopedia
Browse history interactively
← Previous editNext edit →
Content deleted Content added
VisualWikitext
this is notable, it is actually made and sold
Expanded with references
Line 19: Line 19:
| Appearance =
| Appearance =
| Density =
| Density =
| MeltingPt =
| MeltingPt = 60-61 °C
| BoilingPt =
| BoilingPt =
| Solubility =
| Solubility =
Line 30: Line 30:
}}
}}


'''Diphenyl-2-pyridylmethane''' is a [[aryl|triaryl]] [[organic compound]] that has been used to selectively extract specific metal ions (as their [[thiocyanate]] [[Coordination complex|complexes]]) into organic solvents. Its pharmacology is similar to the stimulant [[desoxypipradrol]] in which the [[pyridine]] ring is [[Hydrogenation|reduced]] to a [[piperidine]] and for which it is a chemical precursor.
'''Diphenyl-2-pyridylmethane''' is a stimulant that is related to [[desoxypipradrol]]. A 2012 report by the UK ACMD claimed that "The 2-, 3- and 4- isomers show quite potent activities in binding and uptake assays, with Ki values 0.079 – 0.780 μM in binding and 0.255 – 1.067 μM in inhibition of dopamine reuptake, respectively."<ref name='ACMD official report'>{{cite web | url = http://www.homeoffice.gov.uk/publications/agencies-public-bodies/acmd1/desoxypipradrol-report?view=Standard&pubID=941397 | title = Consideration of Desoxypipradrol (2-DPMP) and related pipradrol compounds | accessdate = 2013-01-10 | date = 2012-09-13 | format = PDF | publisher = UK Home Office}}</ref>
== Preparation ==

Diphenyl-2-pyridylmethane was prepared by researchers at Ciba Pharmaceuticals (now [[Novartis]]) as the immediate precursor of desoxypipradrol, when they patented the latter as a [[psychomotor stimulant]] or [[Narcolepsy|narcoleptic]].<ref>{{cite patent |country=US |number=2820038 |status=patent |gdate=1958-01-14 |fdate=1954-06-11 |pridate=1953-07-06 |invent1 =Hoffmann, K. |invent2 = Heer, J. |invent3 = Sury, E. |invent4 =Urech, E. |title=2-Diphenylmethylpiperidine |assign1=Ciba Pharmaceutical Products |class=C07D211/02 }}</ref><ref>{{cite journal |doi=10.1007/BF02157398 |title=Zentralerregende Wirkung eines neuen Piperidinderivates |year=1954 |last1=Tripod |first1=J. |last2=Sury |first2=E. |last3=Hoffmann |first3=K. |journal=Experientia |volume=10 |issue=6 |pages=261–262 |pmid=13183068 |s2cid=20091456 }}</ref>
Diphenyl acetonitrile was reacted with [[2-bromopyridine]], using [[sodamide]] as base and the resulting diphenyl-2-pyridylacetonitrile was hydrolysed and decarboxylated using potassium hydroxide in methanol.
== Uses ==
Diphenyl-2-pyridylmethane behaves in coordination complexes with metal [[ion|cations]] in the same way as [[pyridine]], with the aromatic nitrogen potentially forming a bond to the metal. In this case, the bulky and [[Lipophilicity|lipophilic]] diphenylmethyl substituent means that the resulting complex may be appreciably soluble in organic solvents like [[chloroform]] and [[benzene]]. This ability to transfer metal cations from water into non-miscible solvents has been exploited to extract thiocyanate complexes for example of silver<ref>{{cite journal |doi=10.1007/BF02060456 |title=Preconcentration and separation of silver from neutron poisons and rare earths using diphenyl-2-pyridylmethane as an extractant |year=1990 |last1=Hasany |first1=S. M. |last2=Ali |first2=A. |journal=Journal of Radioanalytical and Nuclear Chemistry Articles |volume=139 |pages=99–107 |s2cid=97923942 }}</ref>, gold<ref>{{cite journal |doi=10.1007/BF02519409 |title=The extraction of trace amounts of gold from different aqueous mineral acid solutions by diphenyl-2-pyridylmethane dissolved in chloroform |year=1978 |last1=Iqbal |first1=M. |last2=Ejaz |first2=M. |last3=Chaudhri |first3=Shamim A. |last4=Zamiruddin |journal=Journal of Radioanalytical Chemistry |volume=42 |issue=2 |pages=335–348 |s2cid=95227795 }}</ref>, cobalt<ref>{{cite journal |doi=10.1007/BF02516836 |title=Extraction of thiocyanate complexes of cobalt(II) by diphenyl-2-pyridylmethane in benzene from mineral acid solutions |year=1980 |last1=Bhatti |first1=M. S. |last2=Shamasud-Zuha |journal=Journal of Radioanalytical Chemistry |volume=59 |pages=75–81 |s2cid=94128359 }}</ref> and zinc<ref>{{cite journal |doi=10.1007/BF01197227 |title=Diphenyl(2-pyridyl)methane as a solvent for thiocyanate complexes of zinc in aqueous mineral acids |year=1980 |last1=Ejaz |first1=M. |last2=Shamasud-Zuha |last3=Ahmad |first3=Shujaat |last4=Chaudhary |first4=M. Saeed |last5=Rashid |first5=M. |journal=Mikrochimica Acta |volume=73 |issue=1–2 |pages=7–16 |s2cid=92661161 }}</ref>; in some cases in the presence of other metals which were retained in the aqueous phase.
== Pharmacology ==
[[Pipradol]] and desoxypipradrol are [[norepinephrine-dopamine reuptake inhibitor]]s that were not in practice widely used as drugs owing to their perceived potential for abuse. Although diphenyl-2-pyridylmethane is less potent than these molecules and its 4-pyridyl equivalent<ref>{{cite journal |doi=10.1016/S0960-894X(02)00943-5 |title=Pharmacophore-Based discovery of substituted pyridines as novel dopamine transporter inhibitors |year=2003 |last1=Enyedy |first1=Istvan J. |last2=Sakamuri |first2=Sukumar |last3=Zaman |first3=Wahiduz A. |last4=Johnson |first4=Kenneth M. |last5=Wang |first5=Shaomeng |journal=Bioorganic & Medicinal Chemistry Letters |volume=13 |issue=3 |pages=513–517 |pmid=12565962 }}</ref> it was nevertheless specifically included when the UK ACMD advised that this group of drugs be controlled as Class B.<ref name='ACMD official report'>{{cite web | url = http://www.homeoffice.gov.uk/publications/agencies-public-bodies/acmd1/desoxypipradrol-report?view=Standard&pubID=941397 | title = Consideration of Desoxypipradrol (2-DPMP) and related pipradrol compounds | accessdate = 2020-08-25 | date = 2012-09-13 | format = PDF | publisher = UK Home Office}}</ref><ref name="control 2dpmp">{{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 = 2020-08-25 | date = 7 Jun 2012 | publisher = UK Home Office}}</ref>
==See also==
==See also==
*[[Bisacodyl]] (the diacetoxy derivative that is used as a laxative)
*[[Bisacodyl]] (the diacetoxy derivative that is used as a laxative)
Line 38: Line 44:
== References ==
== References ==
{{Reflist}}
{{Reflist}}

{{Stimulants}}
{{Stimulants}}
{{Dopaminergics}}
{{Dopaminergics}}

[[Category:Dopamine reuptake inhibitors]]
[[Category:Dopamine reuptake inhibitors]]
[[Category:Stimulants]]
[[Category:Stimulants]]
[[Category:Pyridines]]
[[Category:Pyridines]]


{{nervous-system-drug-stub}}
{{organic-compound-stub}}

Revision as of 15:30, 25 August 2020

Diphenyl-2-pyridylmethane
Names
IUPAC name
2-(Diphenylmethyl)pyridine
Other names
2-Benzhydrylpyridine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.020.867 Edit this at Wikidata
  • InChI=1S/C18H15N/c1-3-9-15(10-4-1)18(16-11-5-2-6-12-16)17-13-7-8-14-19-17/h1-14,18H
    Key: MMXYNKLYVRNTCK-UHFFFAOYSA-N
  • InChI=1/C18H15N/c1-3-9-15(10-4-1)18(16-11-5-2-6-12-16)17-13-7-8-14-19-17/h1-14,18H
    Key: MMXYNKLYVRNTCK-UHFFFAOYAE
  • n1ccccc1C(c2ccccc2)c3ccccc3
Properties
C18H15N
Molar mass 245.325 g·mol−1
Melting point 60-61 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Diphenyl-2-pyridylmethane is a triaryl organic compound that has been used to selectively extract specific metal ions (as their thiocyanate complexes) 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.

Preparation

Diphenyl-2-pyridylmethane was prepared by researchers at Ciba Pharmaceuticals (now Novartis) as the immediate precursor of desoxypipradrol, when they patented the latter as a psychomotor stimulant or narcoleptic.[1][2] Diphenyl acetonitrile was reacted with 2-bromopyridine, using sodamide as base and the resulting diphenyl-2-pyridylacetonitrile was hydrolysed and decarboxylated using potassium hydroxide in methanol.

Uses

Diphenyl-2-pyridylmethane behaves in coordination complexes with metal cations in the same way as pyridine, with the aromatic nitrogen potentially forming a bond to the metal. In this case, the bulky and lipophilic diphenylmethyl substituent means that the resulting complex may be appreciably soluble in organic solvents like chloroform and benzene. This ability to transfer metal cations from water into non-miscible solvents has been exploited to extract thiocyanate complexes for example of silver[3], gold[4], cobalt[5] and zinc[6]; in some cases in the presence of other metals which were retained in the aqueous phase.

Pharmacology

Pipradol and desoxypipradrol are norepinephrine-dopamine reuptake inhibitors that were not in practice widely used as drugs owing to their perceived potential for abuse. Although diphenyl-2-pyridylmethane is less potent than these molecules and its 4-pyridyl equivalent[7] it was nevertheless specifically included when the UK ACMD advised that this group of drugs be controlled as Class B.[8][9]

See also

References

  1. ^ US patent 2820038, Hoffmann, K.; Heer, J. & Sury, E. et al., "2-Diphenylmethylpiperidine", issued 1958-01-14, assigned to Ciba Pharmaceutical Products 
  2. ^ Tripod, J.; Sury, E.; Hoffmann, K. (1954). "Zentralerregende Wirkung eines neuen Piperidinderivates". Experientia. 10 (6): 261–262. doi:10.1007/BF02157398. PMID 13183068. S2CID 20091456.
  3. ^ Hasany, S. M.; Ali, A. (1990). "Preconcentration and separation of silver from neutron poisons and rare earths using diphenyl-2-pyridylmethane as an extractant". Journal of Radioanalytical and Nuclear Chemistry Articles. 139: 99–107. doi:10.1007/BF02060456. S2CID 97923942.
  4. ^ Iqbal, M.; Ejaz, M.; Chaudhri, Shamim A.; Zamiruddin (1978). "The extraction of trace amounts of gold from different aqueous mineral acid solutions by diphenyl-2-pyridylmethane dissolved in chloroform". Journal of Radioanalytical Chemistry. 42 (2): 335–348. doi:10.1007/BF02519409. S2CID 95227795.
  5. ^ Bhatti, M. S.; Shamasud-Zuha (1980). "Extraction of thiocyanate complexes of cobalt(II) by diphenyl-2-pyridylmethane in benzene from mineral acid solutions". Journal of Radioanalytical Chemistry. 59: 75–81. doi:10.1007/BF02516836. S2CID 94128359.
  6. ^ Ejaz, M.; Shamasud-Zuha; Ahmad, Shujaat; Chaudhary, M. Saeed; Rashid, M. (1980). "Diphenyl(2-pyridyl)methane as a solvent for thiocyanate complexes of zinc in aqueous mineral acids". Mikrochimica Acta. 73 (1–2): 7–16. doi:10.1007/BF01197227. S2CID 92661161.
  7. ^ Enyedy, Istvan J.; Sakamuri, Sukumar; Zaman, Wahiduz A.; Johnson, Kenneth M.; Wang, Shaomeng (2003). "Pharmacophore-Based discovery of substituted pyridines as novel dopamine transporter inhibitors". Bioorganic & Medicinal Chemistry Letters. 13 (3): 513–517. doi:10.1016/S0960-894X(02)00943-5. PMID 12565962.
  8. ^ "Consideration of Desoxypipradrol (2-DPMP) and related pipradrol compounds" (PDF). UK Home Office. 2012-09-13. Retrieved 2020-08-25.
  9. ^ "A Change to the Misuse of Drugs Act 1971: control of pipradrol-related compounds and phenazepam". UK Home Office. 7 Jun 2012. Retrieved 2020-08-25.
Retrieved from "https://en.wikipedia.org/w/index.php?title=Diphenyl-2-pyridylmethane&oldid=974881280"