Pholedrine

Pholedrine
Clinical data
Routes of; administration	Topical (Ocular)
Identifiers
	IUPAC name 4-[2-(Methylamino)propyl]phenol;
CAS Number	370-14-9 ;
PubChem CID	4655;
ChemSpider	4494 ;
UNII	AY28O44JGD;
KEGG	D08370 ;
ChEBI	CHEBI:134798;
ChEMBL	ChEMBL2008672;
ECHA InfoCard	100.006.114
Chemical and physical data
Formula	C10H15NO
Molar mass	165.236 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Oc1ccc(cc1)CC(NC)C;
	InChI InChI=1S/C10H15NO/c1-8(11-2)7-9-3-5-10(12)6-4-9/h3-6,8,11-12H,7H2,1-2H3 ; Key:SBUQZKJEOOQSBV-UHFFFAOYSA-N ;
	(what is this?)

Pholedrine (Paredrinol, Pulsotyl, Veritol), also known as 4-hydroxy-N-methylamphetamine (4-HMA), 4-hydroxymethamphetamine, and para-hydroxymethamphetamine,^[1] is a drug that stimulates the sympathetic nervous system.^[2] It is administered as a topical eye drop form for the purpose of dilating the pupil and can be used to diagnose Horner's syndrome.^[2]

Metabolic pathways of methamphetamine

Methamphetamine

4-Hydroxymethamphetamine

4-Hydroxyphenylacetone

Phenylacetone

Benzoic acid

Hippuric acid

Amphetamine

Norephedrine

4-Hydroxyamphetamine

4-Hydroxynorephedrine

Pholedrine is one of methamphetamine's active metabolites in humans.

References[]

^ P-HYDROXYMETHAMPHETAMINE CAS#: 370-14-9
^ ^a ^b Bates AT, Chamberlain S, Champion M, Foley L, Hughes E, Jani B, et al. (February 1995). "Pholedrine: a substitute for hydroxyamphetamine as a diagnostic eyedrop test in Horner's syndrome". Journal of Neurology, Neurosurgery, and Psychiatry. 58 (2): 215–7. doi:10.1136/jnnp.58.2.215. PMC 1073320. PMID 7876854.

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[1] P-HYDROXYMETHAMPHETAMINE CAS#: 370-14-9

[pmid7876854-2] Bates AT, Chamberlain S, Champion M, Foley L, Hughes E, Jani B, et al. (February 1995). "Pholedrine: a substitute for hydroxyamphetamine as a diagnostic eyedrop test in Horner's syndrome". Journal of Neurology, Neurosurgery, and Psychiatry. 58 (2): 215–7. doi:10.1136/jnnp.58.2.215. PMC 1073320. PMID 7876854.

[1]

[2]

v t Phenethylamines
Phenethylamines	Psychedelics: 25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-C 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-O 2C-O-4 2C-P 2C-SE 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-7 2C-T-8 2C-T-9 2C-T-13 2C-T-15 2C-T-16 2C-T-17 2C-T-19 2C-T-21 2C-T-28 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

Clinical data

Routes of administration	Topical (Ocular)
Identifiers
IUPAC name 4-[2-(Methylamino)propyl]phenol
CAS Number	370-14-9^Y
PubChem CID	4655
ChemSpider	4494^Y
UNII	AY28O44JGD
KEGG	D08370^Y
ChEBI	CHEBI:134798
ChEMBL	ChEMBL2008672
ECHA InfoCard	100.006.114
Chemical and physical data
Formula	C₁₀H₁₅NO
Molar mass	165.236 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES Oc1ccc(cc1)CC(NC)C
InChI InChI=1S/C10H15NO/c1-8(11-2)7-9-3-5-10(12)6-4-9/h3-6,8,11-12H,7H2,1-2H3^N Key:SBUQZKJEOOQSBV-UHFFFAOYSA-N^N
^NY (what is this?)

Pholedrine

See also[]

References[]