4-Methoxyamphetamine is a seratogenic drug of the amphetamine class. The drug acts as a potent and selective serotonin releasing agent. It binds to alpha receptors to mediate these effects.

Target	Actions	Organism
ASodium-dependent dopamine transporter	inhibitor	Humans
ASodium-dependent serotonin transporter	inhibitor	Humans
ASynaptic vesicular amine transporter	inhibitor	Humans
AAlpha-1A adrenergic receptor	agonist	Humans
AAlpha-2A adrenergic receptor	agonist	Humans
UAmine oxidase [flavin-containing] A	inhibitor	Humans
UAmine oxidase [flavin-containing] B	inhibitor	Humans

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Not Available

Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects

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Toxicity

Not Available

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
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1,2-Benzodiazepine	The risk or severity of adverse effects can be increased when 4-Methoxyamphetamine is combined with 1,2-Benzodiazepine.
Abatacept	The metabolism of 4-Methoxyamphetamine can be increased when combined with Abatacept.
Abiraterone	The metabolism of 4-Methoxyamphetamine can be decreased when combined with Abiraterone.
Acebutolol	The therapeutic efficacy of 4-Methoxyamphetamine can be decreased when used in combination with Acebutolol.
Aceclofenac	The risk or severity of hypertension can be increased when 4-Methoxyamphetamine is combined with Aceclofenac.
Acemetacin	The risk or severity of hypertension can be increased when 4-Methoxyamphetamine is combined with Acemetacin.
Acetaminophen	The metabolism of 4-Methoxyamphetamine can be decreased when combined with Acetaminophen.
Acetazolamide	The risk or severity of adverse effects can be increased when Acetazolamide is combined with 4-Methoxyamphetamine.
Acetophenazine	The risk or severity of adverse effects can be increased when Acetophenazine is combined with 4-Methoxyamphetamine.
Acetylsalicylic acid	The risk or severity of hypertension can be increased when Acetylsalicylic acid is combined with 4-Methoxyamphetamine.

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Food Interactions

Not Available

Chemical Identifiers

UNII: OVB8F8P39Q
CAS number: 64-13-1
InChI Key: NEGYEDYHPHMHGK-UHFFFAOYSA-N
InChI: InChI=1S/C10H15NO/c1-8(11)7-9-3-5-10(12-2)6-4-9/h3-6,8H,7,11H2,1-2H3
IUPAC Name: 1-(4-methoxyphenyl)propan-2-amine
SMILES: COC1=CC=C(CC(C)N)C=C1

References

General References

Not Available

External Links

PubChem Compound: 31721
PubChem Substance: 46507471
ChemSpider: 29417
BindingDB: 50024209
ChEMBL: CHEMBL278663
Wikipedia: 4-Methoxyamphetamine

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count

Pharmacoeconomics

Manufacturers: Not Available
Packagers: Not Available
Dosage Forms: Not Available
Prices: Not Available
Patents: Not Available

Properties

State

Solid

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.928 mg/mL	ALOGPS
logP	1.74	ALOGPS
logP	1.65	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Basic)	10.04	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	35.25 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	50.17 m³·mol^-1	ChemAxon
Polarizability	19.29 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.9971
Blood Brain Barrier	+	0.9283
Caco-2 permeable	+	0.7646
P-glycoprotein substrate	Non-substrate	0.688
P-glycoprotein inhibitor I	Non-inhibitor	0.9424
P-glycoprotein inhibitor II	Non-inhibitor	0.9812
Renal organic cation transporter	Non-inhibitor	0.7678
CYP450 2C9 substrate	Non-substrate	0.8422
CYP450 2D6 substrate	Substrate	0.8336
CYP450 3A4 substrate	Non-substrate	0.6008
CYP450 1A2 substrate	Inhibitor	0.6567
CYP450 2C9 inhibitor	Non-inhibitor	0.9747
CYP450 2D6 inhibitor	Inhibitor	0.8492
CYP450 2C19 inhibitor	Non-inhibitor	0.6537
CYP450 3A4 inhibitor	Non-inhibitor	0.9431
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.8424
Ames test	Non AMES toxic	0.6201
Carcinogenicity	Non-carcinogens	0.8044
Biodegradation	Not ready biodegradable	0.875
Rat acute toxicity	2.8848 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.8836
hERG inhibition (predictor II)	Non-inhibitor	0.8576

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

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Spectra

Spectrum	Spectrum Type	Splash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available

Targets

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Details1. Sodium-dependent dopamine transporter

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Inhibitor

General Function: Monoamine transmembrane transporter activity
Specific Function: Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name: SLC6A3
Uniprot ID: Q01959
Uniprot Name: Sodium-dependent dopamine transporter
Molecular Weight: 68494.255 Da

References

Daws LC, Irvine RJ, Callaghan PD, Toop NP, White JM, Bochner F: Differential behavioural and neurochemical effects of para-methoxyamphetamine and 3,4-methylenedioxymethamphetamine in the rat. Prog Neuropsychopharmacol Biol Psychiatry. 2000 Aug;24(6):955-77. [Article]
Hansen JP, Riddle EL, Sandoval V, Brown JM, Gibb JW, Hanson GR, Fleckenstein AE: Methylenedioxymethamphetamine decreases plasmalemmal and vesicular dopamine transport: mechanisms and implications for neurotoxicity. J Pharmacol Exp Ther. 2002 Mar;300(3):1093-100. [Article]
Fitzgerald JL, Reid JJ: Effects of methylenedioxymethamphetamine on the release of monoamines from rat brain slices. Eur J Pharmacol. 1990 Nov 27;191(2):217-20. [Article]
Fleckenstein AE, Volz TJ, Riddle EL, Gibb JW, Hanson GR: New insights into the mechanism of action of amphetamines. Annu Rev Pharmacol Toxicol. 2007;47:681-98. [Article]

Details2. Sodium-dependent serotonin transporter

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Inhibitor

General Function: Serotonin:sodium symporter activity
Specific Function: Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into t...
Gene Name: SLC6A4
Uniprot ID: P31645
Uniprot Name: Sodium-dependent serotonin transporter
Molecular Weight: 70324.165 Da

References

Daws LC, Irvine RJ, Callaghan PD, Toop NP, White JM, Bochner F: Differential behavioural and neurochemical effects of para-methoxyamphetamine and 3,4-methylenedioxymethamphetamine in the rat. Prog Neuropsychopharmacol Biol Psychiatry. 2000 Aug;24(6):955-77. [Article]
Shankaran M, Yamamoto BK, Gudelsky GA: Involvement of the serotonin transporter in the formation of hydroxyl radicals induced by 3,4-methylenedioxymethamphetamine. Eur J Pharmacol. 1999 Dec 3;385(2-3):103-10. [Article]
Whitworth TL, Herndon LC, Quick MW: Psychostimulants differentially regulate serotonin transporter expression in thalamocortical neurons. J Neurosci. 2002 Jan 1;22(1):RC192. [Article]
Szabo Z, McCann UD, Wilson AA, Scheffel U, Owonikoko T, Mathews WB, Ravert HT, Hilton J, Dannals RF, Ricaurte GA: Comparison of (+)-(11)C-McN5652 and (11)C-DASB as serotonin transporter radioligands under various experimental conditions. J Nucl Med. 2002 May;43(5):678-92. [Article]
Boot BP, Mechan AO, McCann UD, Ricaurte GA: MDMA- and p-chlorophenylalanine-induced reduction in 5-HT concentrations: effects on serotonin transporter densities. Eur J Pharmacol. 2002 Oct 25;453(2-3):239-44. [Article]
Saldana SN, Barker EL: Temperature and 3,4-methylenedioxymethamphetamine alter human serotonin transporter-mediated dopamine uptake. Neurosci Lett. 2004 Jan 16;354(3):209-12. [Article]
Bogen IL, Haug KH, Myhre O, Fonnum F: Short- and long-term effects of MDMA ("ecstasy") on synaptosomal and vesicular uptake of neurotransmitters in vitro and ex vivo. Neurochem Int. 2003 Sep-Oct;43(4-5):393-400. [Article]

Details3. Synaptic vesicular amine transporter

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Inhibitor

General Function: Monoamine transmembrane transporter activity
Specific Function: Involved in the ATP-dependent vesicular transport of biogenic amine neurotransmitters. Pumps cytosolic monoamines including dopamine, norepinephrine, serotonin, and histamine into synaptic vesicles...
Gene Name: SLC18A2
Uniprot ID: Q05940
Uniprot Name: Synaptic vesicular amine transporter
Molecular Weight: 55712.075 Da

References

Biezonski DK, Meyer JS: Effects of 3,4-methylenedioxymethamphetamine (MDMA) on serotonin transporter and vesicular monoamine transporter 2 protein and gene expression in rats: implications for MDMA neurotoxicity. J Neurochem. 2010 Feb;112(4):951-62. doi: 10.1111/j.1471-4159.2009.06515.x. Epub 2009 Nov 30. [Article]
Hansen JP, Riddle EL, Sandoval V, Brown JM, Gibb JW, Hanson GR, Fleckenstein AE: Methylenedioxymethamphetamine decreases plasmalemmal and vesicular dopamine transport: mechanisms and implications for neurotoxicity. J Pharmacol Exp Ther. 2002 Mar;300(3):1093-100. [Article]

Details4. Alpha-1A adrenergic receptor

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Agonist

General Function: Protein heterodimerization activity
Specific Function: This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
Gene Name: ADRA1A
Uniprot ID: P35348
Uniprot Name: Alpha-1A adrenergic receptor
Molecular Weight: 51486.005 Da

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]

Details5. Alpha-2A adrenergic receptor

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Agonist

General Function: Thioesterase binding
Specific Function: Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazo...
Gene Name: ADRA2A
Uniprot ID: P08913
Uniprot Name: Alpha-2A adrenergic receptor
Molecular Weight: 48956.275 Da

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]

Details6. Amine oxidase [flavin-containing] A

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Serotonin binding
Specific Function: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral...
Gene Name: MAOA
Uniprot ID: P21397
Uniprot Name: Amine oxidase [flavin-containing] A
Molecular Weight: 59681.27 Da

References

Green AL, El Hait MA: p-Methoxyamphetamine, a potent reversible inhibitor of type-A monoamine oxidase in vitro and in vivo. J Pharm Pharmacol. 1980 Apr;32(4):262-6. [Article]
Ask AL, Fagervall I, Ross SB: Selective inhibition of monoamine oxidase in monoaminergic neurons in the rat brain. Naunyn Schmiedebergs Arch Pharmacol. 1983 Sep;324(2):79-87. [Article]

Details7. Amine oxidase [flavin-containing] B

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Primary amine oxidase activity
Specific Function: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral...
Gene Name: MAOB
Uniprot ID: P27338
Uniprot Name: Amine oxidase [flavin-containing] B
Molecular Weight: 58762.475 Da

References

Green AL, El Hait MA: p-Methoxyamphetamine, a potent reversible inhibitor of type-A monoamine oxidase in vitro and in vivo. J Pharm Pharmacol. 1980 Apr;32(4):262-6. [Article]
Ask AL, Fagervall I, Ross SB: Selective inhibition of monoamine oxidase in monoaminergic neurons in the rat brain. Naunyn Schmiedebergs Arch Pharmacol. 1983 Sep;324(2):79-87. [Article]

Enzymes

Details1. Cytochrome P450 2D6

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Steroid hydroxylase activity
Specific Function: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name: CYP2D6
Uniprot ID: P10635
Uniprot Name: Cytochrome P450 2D6
Molecular Weight: 55768.94 Da

References

Wu D, Otton SV, Inaba T, Kalow W, Sellers EM: Interactions of amphetamine analogs with human liver CYP2D6. Biochem Pharmacol. 1997 Jun 1;53(11):1605-12. [Article]
Flockhart Table of Drug Interactions [Link]

Drug created on June 13, 2005 13:24 / Updated on June 12, 2020 16:51

4-Methoxyamphetamine

Identification

Structure for 4-Methoxyamphetamine (DB01472)

Pharmacology

Interactions

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Targets

References

References

References

References

References

References

References

Enzymes

References