Pyridoxiphen

Pyridoxiphen, also known as amphetamine–pyridoxine condensation product or as pyridoxylamphetamine, is a drug of the substituted amphetamine family which was developed in the Soviet Union in the 1960s.^[1]^[2]^[3]^[4]^[5]^[6] It is the condensation product of amphetamine (phenamine) and pyridoxine (vitamin B₆).^[2] It was developed for potential treatment of central nervous system conditions.^[2] The drug has sympatholytic and hypotensive effects in animals.^[7]^[1]^[6]^[8] It is highly ionic and may not be able to cross the blood–brain barrier.^[7]

Other namesAmphetamine–pyridoxine condensation product; Phenamine–pyridoxine condensation product; Pyridoxyphen; Pyridoxiphene; Piridoksifen; Piridoksifena; Pyridoxylamphetamine

PubChem CID

121419

ChemSpider

108374

FormulaC₁₇H₂₂N₂O₂

Quick facts Clinical data, Other names ...

Pyridoxiphen
Clinical data

Other names	Amphetamine–pyridoxine condensation product; Phenamine–pyridoxine condensation product; Pyridoxyphen; Pyridoxiphene; Piridoksifen; Piridoksifena; Pyridoxylamphetamine
Identifiers
IUPAC name 4-(hydroxymethyl)-2-methyl-5-[(1-phenylpropan-2-ylamino)methyl]pyridin-3-ol
PubChem CID	121419
ChemSpider	108374
Chemical and physical data
Formula	C₁₇H₂₂N₂O₂
Molar mass	286.375 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC1=NC=C(C(=C1O)CO)CNC(C)CC2=CC=CC=C2
InChI InChI=1S/C17H22N2O2/c1-12(8-14-6-4-3-5-7-14)18-9-15-10-19-13(2)17(21)16(15)11-20/h3-7,10,12,18,20-21H,8-9,11H2,1-2H3 Key:UDDSBCOQRRHWBZ-UHFFFAOYSA-N

References

[1]
Jablonski S (1967). Russian Drug Index. Public Health Service publication. U.S. Department of Health, Education, and Welfare, Public Health Service. p. 245. Retrieved 4 October 2024 – via National Library of Medicine (U.S.). Pyridoxiphen (Piridoksifen). 4-Pyridinemethanol, 3-hydroxy-2-methyl-5-((α-methylphenethyl)amino)methyl)-, dihydrochloride. C17H22N2O2.2HCl. [Structure image.] Product of condensation of phenamine and pyridoxine.. Arbuzov SI, Smirnova SM 1964; Arbuzov SI, Smirnova SM (1964). "Sympatholytic and hypotensive effects of pyridoxiphen". Farmakologiia i Toksikologiia. 27: 420–423. PMID 14193108.
[2]
Dange SA, Adhikari GM (1963). International Socialist Miscellany (in Italian). p. 131. Retrieved 4 October 2024. Our chair has also produced certain derivatives of phenatin which likewise possess valuable qualities. For instance, there is pyridoxiphen, a product of condensation of phenamin and pyridoxine (Vitamin B3). This preparation is necessary in clinical practice for treating some of the diseases of the nervous system. We are persistently looking for even more active stimulators. This calls for a still deeper knowledge of the processes of metabolism in the nervous tissues, processes that lead to the exhaustion of these tissues, This will provide man with a means of conquering fatigue for long.
[3]
Marler EE (1983). Pharmacological and Chemical Synonyms: A Collection of Names of Drugs, Pesticides and Other Compounds Drawn from the Medical Literature of the World. Excerpta Medica. pp. 30, 419. ISBN 978-90-219-3061-9. Retrieved 4 October 2024. PYRIDOXIPHEN (tr) (amphetamine-pyridoxine condensation product)
[4]
Arbuzov SI, Aleksandrova AE, Amirnova SM (1966). "[On the action of pyridoxyphen on central nervous system]" [On the action of pyridoxyphen on central nervous system]. Farmakologiia i Toksikologiia (in Russian). 29 (5): 521–522. PMID 5995060.
[5]
Arbuzov SI, Gorodnik AG, Nikiforov MI (1968). "[On the effect of pyridoxiphen on some functions of the nervous system]" [On the effect of pyridoxiphen on some functions of the nervous system]. Farmakologiia i Toksikologiia (in Russian). 31 (2): 152–156. PMID 5674665.
[6]
Aerospace Technology Division, Library of Congress. "CBE Factors Monthly Survey No. 40, ATD Work Assignment No. 50 (ATD Report 69-77-50-10)" (PDF). Retrieved 4 October 2024. Compound I does not display the pronounced hypotensive action characteristic of Pirodoksifen (i.e., pyridoxylamphetamine) and Fenatin (i.e., nicotinoylamphetamine) nor the central stimulating effect of Fenatin.
[7]
Fitzpatrick WH (1974). Soviet Research in Pharmacology and Toxicology, 1963-1972. DHEW publication no. (NIH) 75-696. National Institutes of Health. pp. 22, 77. Retrieved 4 October 2024. C. Other Drug Effects (32) investigated the action of Arbuzov, Aleksandrova et al. pyridoxyphen, a new adrenolytic, on the central nervous system. Pyridoxyphen, a product of the condensation of phenamine and pyridoxine, exerted no central adrenolytic action. Because of the highly ionic nature of the molecule, the authors concluded that pyridoxyphen was incapable of overcoming the hemato-encephalic barrier.
[8]
Arbuzov SI, Smirnova SM (1964). "Simpatoliticheskoe i gipotenzivnoe de istvie piridoksifena" [Sympatholytic and hypotensive effects of pyridoxiphen]. Farmakologiia i Toksikologiia (in Russian). 27: 420–423. PMID 14193108.

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