NAV

4-Methoxyamphetamine

Identification

Generic Name
4-Methoxyamphetamine
DrugBank Accession Number
DB01472
Background

Not Available

Type
Small Molecule
Groups
Experimental, Illicit
Structure
3D
Similar Structures
Weight
Average: 165.2322
Monoisotopic: 165.115364107
Chemical Formula
C10H15NO
Synonyms
  • (2RS)-1-(4-methoxyphenyl)propan-2-amine
  • 4-methoxyamfetamine
  • D,L-p-methoxyamphetamine
  • Formoterol fumarate related compound G
  • P-methoxyamfetamine
  • P-methoxyamphetamine
  • Paramethoxyamphetamine
External IDs
  • J213.549C
  • J434.573H
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action

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.

TargetActionsOrganism
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.
DrugInteraction
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1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when 4-Methoxyamphetamine is combined with 1,2-Benzodiazepine.
AbataceptThe metabolism of 4-Methoxyamphetamine can be increased when combined with Abatacept.
AbirateroneThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Abiraterone.
AcebutololThe therapeutic efficacy of 4-Methoxyamphetamine can be decreased when used in combination with Acebutolol.
AceclofenacThe risk or severity of hypertension can be increased when 4-Methoxyamphetamine is combined with Aceclofenac.
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenethylamines
Direct Parent
Amphetamines and derivatives
Alternative Parents
Phenylpropanes / Phenoxy compounds / Methoxybenzenes / Anisoles / Aralkylamines / Alkyl aryl ethers / Organopnictogen compounds / Monoalkylamines / Hydrocarbon derivatives
Substituents
Alkyl aryl ether / Amine / Amphetamine or derivatives / Anisole / Aralkylamine / Aromatic homomonocyclic compound / Ether / Hydrocarbon derivative / Methoxybenzene / Organic nitrogen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
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
PubChem Compound
31721
PubChem Substance
46507471
ChemSpider
29417
BindingDB
50024209
ChEMBL
CHEMBL278663
Wikipedia
4-Methoxyamphetamine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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
PropertyValueSource
Water Solubility0.926 mg/mLALOGPS
logP1.74ALOGPS
logP1.65Chemaxon
logS-2.2ALOGPS
pKa (Strongest Basic)10.04Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area35.25 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity50.17 m3·mol-1Chemaxon
Polarizability19.29 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9971
Blood Brain Barrier+0.9283
Caco-2 permeable+0.7646
P-glycoprotein substrateNon-substrate0.688
P-glycoprotein inhibitor INon-inhibitor0.9424
P-glycoprotein inhibitor IINon-inhibitor0.9812
Renal organic cation transporterNon-inhibitor0.7678
CYP450 2C9 substrateNon-substrate0.8422
CYP450 2D6 substrateSubstrate0.8336
CYP450 3A4 substrateNon-substrate0.6008
CYP450 1A2 substrateInhibitor0.6567
CYP450 2C9 inhibitorNon-inhibitor0.9747
CYP450 2D6 inhibitorInhibitor0.8492
CYP450 2C19 inhibitorNon-inhibitor0.6537
CYP450 3A4 inhibitorNon-inhibitor0.9431
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8424
Ames testNon AMES toxic0.6201
CarcinogenicityNon-carcinogens0.8044
BiodegradationNot ready biodegradable0.875
Rat acute toxicity2.8848 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8836
hERG inhibition (predictor II)Non-inhibitor0.8576
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (8.19 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00kb-1900000000-cce1b8a57f01827c7be6
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03k9-0900000000-989abcf351827d0c5fde
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-7900000000-eba1eb99a3be7690c91f
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-006x-4900000000-47431390c930a4a11719
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-004l-9300000000-9cb595bd7c7a20e5feae
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9500000000-1ef0928d41d1370f01eb
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-136.63448
predicted
DeepCCS 1.0 (2019)
[M+H]+140.46182
predicted
DeepCCS 1.0 (2019)
[M+Na]+149.7339
predicted
DeepCCS 1.0 (2019)

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
  1. 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]
  2. 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]
  3. 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]
  4. 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
  1. 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]
  2. 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]
  3. Whitworth TL, Herndon LC, Quick MW: Psychostimulants differentially regulate serotonin transporter expression in thalamocortical neurons. J Neurosci. 2002 Jan 1;22(1):RC192. [Article]
  4. 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]
  5. 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]
  6. 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]
  7. 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
  1. 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]
  2. 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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. 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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. 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
  1. 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]
  2. 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
  1. 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]
  2. 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
  1. 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]
  2. Flockhart Table of Drug Interactions [Link]

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