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4-hydroxy Amphetamine (hydrochloride)

Item No. 9001830

Product Insert (PDF)GC-MS (PDF)Safety Data Sheet (SDS) (PDF)
Synonyms
Synonyms
  • 4-HA
  • α-methyl Tyramine
  • p-hydroxy Amphetamine
  • para-hydroxy Amphetamine
  • Paredrine
  • POHA
Technical Information
Formal Name
4-(2-aminopropyl)-phenol, monohydrochloride
CAS Number
876-26-6
Molecular Formula
C9H13NO • HCl
Formula Weight
187.7
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/mlPBS (pH 7.2): 10 mg/ml
λmax
226, 278 nm
SMILES
OC1=CC=C(CC(C)N)C=C1.Cl
InChi Code
InChI=1S/C9H13NO.ClH/c1-7(10)6-8-2-4-9(11)5-3-8;/h2-5,7,11H,6,10H2,1H3;1H
InChi Key
MYTMYIPUXIMVQW-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    4-Hydroxyamphetamine (4-HA) is a bioactive metabolite of amphetamine.1,2 This sympathomimetic is an agonist of the trace amine-associated receptor 1 (EC50 = ~0.2 μM in HEK293 cells expressing rat TAAR1).3 As a 1% ophthalmologic solution, 4-HA has been used to dilate the pupil in the diagnosis of Horner’s syndrome.4,5 This product is intended only for forensic and research purposes.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hermanson, D.J., Hartley, N.D., Gamble-George, J., et al. Substrate-selective COX-2 inhibition decreases anxiety via endocannabinoid activation. Nat. Neurosci. 16(9), 1291-1298 (2013).

    2. Liu, F., Boross, P.I., Wang, Y.F., et al. Kinetic, stability, and structural changes in high-resolution crystal structures of HIV-1 protease with drug-resistant mutations L24I, I50V, and G73S. J. Mol. Biol. 354(4), 789-800 (2005).

    3. Dorsey, B.D., McDonough, C., McDaniel, S.L., et al. Identification of MK-944a: A second clinical candidate from the hydroxylaminepentanamide isostere series of HIV protease inhibitors. J. Med. Chem. 43(18), 3386-3399 (2000).

    4. Dolle, R.E., Hoyer, D., Prasad, C.V.C., et al. P1 aspartate-based peptide α-((2,6dichlorobenzoyl)oxy)methyl ketones as potent time-dependent inhibitors of interleukin-1β-converting enzyme. J. Med. Chem. 37(5), 563-564 (1994).

    5. Kalbhen, D.A. Nutmeg as a narcotic. A contribution to the chemistry and pharmacology of nutmeg. Angew. Chem. Int. Ed. Engl. 10(6), 370-374 (1971).