Pyridoxiphen

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;

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 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]

References

^ ^a ^b Jablonski, S.; National Library of Medicine (U.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. 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, S. Ia., & Smirnova, S. M. "Sympatholytic and hypotensive effects of pyridoxiphen" Farmakol Toksik, 1964, 27: No. 4, p. 420-3.
^ ^a ^b ^c Dange, S.A.; Adhikari, G.M. (1963). International Socialist Miscellany (in Italian). S.A. Dange and G. Adhikari. 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.
^ Marler, E.E.J. (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)
^ Arbuzov SI, Aleksandrova AE, Amirnova SM (1966). "O vliianii piridoksifena na tsentral'nyiu nervnuiu sistemu" [On the action of pyridoxyphen on central nervous system]. Farmakol Toksikol (in Russian). 29 (5): 521–522. PMID 5995060.
^ Arbuzov SI, Gorodnik AG, Nikiforov MI (1968). "O vliianii piridoksifena na nekotorye funktsii nervnoĭ sistmey" [On the effect of pyridoxiphen on some functions of the nervous system]. Farmakol Toksikol (in Russian). 31 (2): 152–156. PMID 5674665.
^ ^a ^b 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.
^ ^a ^b Fitzpatrick, W.H. (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.
^ Arbuzov SI, Smirnova SM (1964). "Simpatoliticheskoe i gipotenzivnoe de istvie piridoksifena" [Sympatholytic and hypotensive effects of pyridoxiphen]. Farmakol Toksikol (in Russian). 27: 420–423. PMID 14193108.

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[JablonskiNLM1967-1] Jablonski, S.; National Library of Medicine (U.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. 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, S. Ia., & Smirnova, S. M. "Sympatholytic and hypotensive effects of pyridoxiphen" Farmakol Toksik, 1964, 27: No. 4, p. 420-3.

[DangeAdhikari1963-2] Dange, S.A.; Adhikari, G.M. (1963). International Socialist Miscellany (in Italian). S.A. Dange and G. Adhikari. 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.

[Marler1983-3] Marler, E.E.J. (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)

[ArbuzovAleksandrovaAmirnova1966-4] Arbuzov SI, Aleksandrova AE, Amirnova SM (1966). "O vliianii piridoksifena na tsentral'nyiu nervnuiu sistemu" [On the action of pyridoxyphen on central nervous system]. Farmakol Toksikol (in Russian). 29 (5): 521–522. PMID 5995060.

[ArbuzovGorodnikNikiforov1968-5] Arbuzov SI, Gorodnik AG, Nikiforov MI (1968). "O vliianii piridoksifena na nekotorye funktsii nervnoĭ sistmey" [On the effect of pyridoxiphen on some functions of the nervous system]. Farmakol Toksikol (in Russian). 31 (2): 152–156. PMID 5674665.

[ATDReport69-77-50-10-6] 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.

[Fitzpatrick1974-7] Fitzpatrick, W.H. (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.

[ArbuzovSmirnova1964-8] Arbuzov SI, Smirnova SM (1964). "Simpatoliticheskoe i gipotenzivnoe de istvie piridoksifena" [Sympatholytic and hypotensive effects of pyridoxiphen]. Farmakol Toksikol (in Russian). 27: 420–423. PMID 14193108.

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v t e Phenethylamines
Phenethylamines	Psychedelics: 25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-B-AN 2C-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-G-1 2C-G-2 2C-G-3 2C-G-4 2C-G-5 2C-G-6 2C-G-N 2C-H 2C-I 2C-iP 2C-N 2C-NH2 2C-O 2C-O-4 2C-P 2C-Ph 2C-SE 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-5 2C-T-6 2C-T-7 2C-T-8 2C-T-9 2C-T-10 2C-T-11 2C-T-12 2C-T-13 2C-T-14 2C-T-15 2C-T-16 2C-T-17 2C-T-18 2C-T-19 2C-T-20 2C-T-21 2C-T-22 2C-T-22.5 2C-T-23 2C-T-24 2C-T-25 2C-T-27 2C-T-28 2C-T-30 2C-T-31 2C-T-32 2C-T-33 2C-TFE 2C-TFM 2C-YN 2C-V Allylescaline DESOXY Escaline Isoproscaline Jimscaline Macromerine MEPEA Mescaline Metaescaline Methallylescaline Proscaline Psi-2C-T-4 TCB-2 Stimulants: Phenylethanolamine Hordenine Phenethylamine Phenpromethamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Methylphenidate Entactogens: Lophophine MDPEA MDMPEA Others: BOH DMPEA
Amphetamines	Psychedelics: 3C-AL 3C-BZ 3C-E 3C-MAL 3C-P Aleph Beatrice Bromo-DragonFLY D-Deprenyl DMA DMCPA DMMDA DOB DOC DOEF DOET DOI DOM DON DOPR DOTFM Ganesha MMDA MMDA-2 Psi-DOM TMA TeMA ZDCM-04 Stimulants: 2-FA 2-FMA 3-FA 3-FMA Acridorex Alfetamine Amfecloral Amfepentorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Benfluorex Benzphetamine Cathine Clobenzorex Dimethylamphetamine Ephedrine Etilamfetamine Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Flucetorex Fludorex Formetorex Furfenorex Gepefrine 4-Hydroxyamphetamine Iofetamine Isopropylamphetamine Lefetamine Lisdexamfetamine Mefenorex Metaraminol Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxyphenamine MMA Morforex Norfenfluramine L-Norpseudoephedrine N,alpha-Diethylphenylethylamine Oxifentorex Oxilofrine Ortetamine PBA PCA PFA PFMA PIA PMA PMEA PMMA Phenylpropanolamine Pholedrine Prenylamine Propylamphetamine Pseudoephedrine Sibutramine Tiflorex Tranylcypromine Xylopropamine Zylofuramine Entactogens: 4-FA 4-FMA 4-MA 4-MMA 4-MTA 5-APB 5-APDB 5-EAPB 5-IT 5-MAPB 5-MAPDB 6-APB 6-APDB 6-Chloro-MDMA 6-EAPB 6-IT 6-MAPB 6-MAPDB EDA IAP 2,3-MDA 3,4-MDA (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) MDOH Methamnetamine MMDMA Naphthylaminopropane TAP Others: 3,4-DCA Amiflamine DiFMDA Selegiline (also D-Deprenyl)
Phentermines	Stimulants: Chlorphentermine Cloforex Clortermine Etolorex Mephentermine Pentorex Phentermine Entactogens: MDPH MDMPH Others: Cericlamine
Cathinones	Stimulants: 3-FMC 4-MC 4-BMC 4-CMC 4-EMC 4-FMC 4-MEC 4-MeMABP 4-MPD Amfepramone Benzedrone Brephedrone Buphedrone Bupropion Cathinone Dimethylcathinone Ethcathinone Eutylone Hydroxybupropion Methcathinone Methedrone NEB N-Ethylhexedrone N-Ethylpentedrone Pentedrone Pentylone Radafaxine Entactogens: 3,4-DMMC 3-MMC Butylone Ethylone Methylone Methylenedioxycathinone Mephedrone
Phenylisobutylamines	Entactogens: 4-CAB 4-MAB Ariadne BDB Butylone EBDB Eutylone MBDB Stimulants: Phenylisobutylamine
Phenylalkylpyrrolidines	Stimulants: α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP MOPPP MOPVP MPBP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone
Catecholamines (and close relatives)	6-FNE 6-OHDA a-Me-DA a-Me-TRA Adrenochrome Ciladopa D-DOPA (Dextrodopa) Dimetofrine Dopamine Epinephrine Epinine Etilefrine Ethylnorepinephrine Fenclonine Ibopamine Isoprenaline Isoetarine L-DOPA (Levodopa) L-DOPS (Droxidopa) L-Phenylalanine L-Tyrosine m-Tyramine Metanephrine Metaraminol Metaterol Metirosine Methyldopa N,N-Dimethyldopamine Nordefrin (Levonordefrin) Norepinephrine Norfenefrine (m-Octopamine) Normetanephrine Orciprenaline p-Octopamine p-Tyramine Phenylephrine Synephrine
Miscellaneous	AL-LAD Amidephrine Arbutamine Cafedrine Denopamine Desvenlafaxine Diphenidine Dizocilpine Dobutamine Dopexamine Ephenidine Etafedrine ETH-LAD Famprofazone Fluorolintane Hexapradol IP-LAD Lysergic acid amide Lysergic acid 2-butyl amide Lysergic acid 2,4-dimethylazetidide Lysergic acid diethylamide Methoxamine Methoxphenidine MT-45 PARGY-LAD Phenibut PRO-LAD Pronethalol Salbutamol (Levosalbutamol) Solriamfetol Theodrenaline Thiamphenicol UWA-101 Venlafaxine

See also

References