Oxilofrine (4-HEP)

4-HEP

Molecular structure via molpic based on CDK

Conformer []

Conformer structure via JSmol

Physical properties []
Molecular mass	181.23 g/mol ^[1]
Solubility	Partly miscible ^[1]
Predicted LogP	0.6 ^[1]

Structural Identifiers []
Molecular formula	C₁₀H₁₅NO₂ ^[1]
IUPAC name	4-[(1R,2S)-1-hydroxy-2-(methylamino)propyl]phenol ^[1]
SMILES	C[C@@H]([C@@H](C1=CC=C(C=C1)O)O)NC ^[1]
InChI	InChI=1S/C10H15NO2/c1-7(11-2)10(13)8-3-5-9(12)6-4-8/h3-7,10-13H,1-2H3/t7-,10-/m0/s1 ^[1]
InChIKey	OXFGTKPPFSCSMA-XVKPBYJWSA-N ^[1]

Oxilofrine

Oxilofrine (also known as Methylsynephrin, Methylsympatol, Oxyephedrin, Methyl synephrin, Methyl synephrine, p-Hydroxyephedrine, Oxilofrinum, Oxyephedrine, Oxilofrina or Suprifene) is a sympathomimetic substance of the phenylethanolamine class.

Chemistry

Salts []

Oxilofrine is typically found in the form of its hydrochloride salt.

Stereochemistry []

(RS)-Oxilofrine is a racemic mixture of the optical stereoisomers

Subjective effects []

Physical effects
Abnormal heartbeat Dehydration Dry mouth Increased blood pressure Increased heart rate Restless legs Shakiness Stamina enhancement Vasoconstriction

Cognitive effects
Thought acceleration Wakefulness

Legal status []

Brazil: Oxilofrine is a A3 substance.^[3]
United States: Oxilofrine is a Unapproved "New Drug" (as defined by 21 U.S. Code § 321(p)(1)). Use in dietary supplements, food, or medicine is unlawful; otherwise uncontrolled. substance.^[4]

External links []

References []

National Center for Biotechnology Information. PubChem Compound Summary for CID 688009, Oxilofrine. Accessed June 26, 2025. https://pubchem.ncbi.nlm.nih.gov/compound/688009
U.S. Food and Drug Administration; National Center for Advancing Translational Sciences. Oxilofrine. UNII: F49638UBDR. Global Substance Registration System. Accessed June 26, 2025. https://gsrs.ncats.nih.gov/ginas/app/beta/substances/F49638UBDR
Anvisa. RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial. Diário Oficial da União. March 31, 2023. Accessed June 26, 2025. https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992
Methylsynephrine in Dietary Supplements. February 22, 2023. Accessed June 26, 2025. https://www.fda.gov/food/dietary-supplement-ingredient-directory/methylsynephrine-dietary-supplements

Anodyne