Methoxamine

Not to be confused with methoxetamine.

Methoxamine

File:Methoxamine.png
Systematic (IUPAC) name
2-amino-1-(2,5-dimethoxyphenyl)propan-1-ol
Clinical data
AHFS/Drugs.com	International Drug Names
Legal status	Experimental (Unlicensed)
Dependence liability	Low (when administered as prescribed) High (when misused in either higher doses or injected repeatedly)
Routes of administration	Intravenous, intramuscular, sublingual, subcutaneous, transdermal.
Pharmacokinetic data
Bioavailability	21% (sublingually), 93% (intramuscularly), 4% (oral), 78% transdermal
Metabolism	CYPD26 (cytochrome p450) (hepatic)
Biological half-life	18.6 hours (M1 metabolite 45 hours)
Excretion	renal
Identifiers
CAS Number	390-28-3 Y
ATC code	C01CA10 (WHO)
PubChem	CID: 6082
IUPHAR/BPS	483
DrugBank	DB00723 N
ChemSpider	5857 Y
UNII	HUQ1KC1YLI Y
KEGG	D08201 Y
ChEMBL	CHEMBL524 Y
Chemical data
Formula	C11H17NO3
Molecular mass	211.258
SMILES O(c1ccc(OC)cc1C(O)C(N)C)C
InChI InChI=1S/C11H17NO3/c1-7(12)11(13)9-6-8(14-2)4-5-10(9)15-3/h4-7,11,13H,12H2,1-3H3 Y Key:WJAJPNHVVFWKKL-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Methoxamine Hydrochloride is an α₁-adrenergic receptor agonist, SNRI, MDMA agonist somewhat similar in structure to butaxamine and 2,5-DMA. It was first theorised and synthesised by British pharmacologist Oliver Ansell in 2015 and then patented on January 4, 2016. The compound has been accepted for preliminary clinical trials. Methoxamine is a theoretical novel fast-acting antidepressant with mood lifting qualities that may alleviate the symptoms of clinical depression as an ultra-fast onset agent, in comparison to SSRIs, MAOIs and even tricyclic and tetracyclic antidepressants. Which all have a significantly long period of time for the optimum peak blood concentration is attained, commonly leading to patients to discontinue their treatment and can also induce suicidal ideation.

This is not the case with Methoxamine, as it readily crosses the blood brain barrier and stimulates the release of serotonin, inhibits the re-uptake of norepinephrine. Mood lift is also expected to be enhanced by the M1 metabolite, which weakly binds to μ-opioid receptors (approximate potency is comparable of that of dextropropoxyphene.but at proper prescribed doses and time frames there is a very low risk of this causing any dependency or tolerance to the effect)

Methoxamine in Clinical Trials

File:Methoxamine in it's current manufactured form in a solution in both a syringe and vial..jpg

Methoxamine HCl shown here in its pre-market manufactured state for early phase clinical research.

For example, a standard sublingual dose of 15 mg would be equipotent between 5–25 mg of dextropropoxyphene depending on the metabolism of the individual. Although this in no way implies that methoxamine or its metabolites resemble dextropropoxyphene, it is simply a weak opioid from which an easy comparison can be drawn.

The drug occasionally induces slight vasoconstriction of skin and splanchnic blood vessels, thereby increasing peripheral vascular resistance and raising mean arterial blood pressure. Because of its hypertensive effects, it may evoke a compensatory reflex bradycardia via the baroreceptors.

See also

• Sertraline
• Phenylephrine
• Synephrine