2,4,5-Trimethoxyamphetamine

ID: ALA8389

Max Phase: Preclinical

Molecular Formula: C12H19NO3

Molecular Weight: 225.29

Molecule Type: Small molecule

Associated Items:

Representations

Canonical SMILES:  COc1cc(OC)c(OC)cc1CC(C)N

Standard InChI:  InChI=1S/C12H19NO3/c1-8(13)5-9-6-11(15-3)12(16-4)7-10(9)14-2/h6-8H,5,13H2,1-4H3

Standard InChI Key:  TVSIMAWGATVNGK-UHFFFAOYSA-N

Associated Targets(Human)

Homo sapiens (32628 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR2A Tclin Serotonin 2a (5-HT2a) receptor (14758 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Htr1b Serotonin 1 (5-HT1) receptor (408 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Htr2b Serotonin 2 (5-HT2) receptor (2078 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Htr3a Serotonin (5-HT) receptor (353 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Rattus norvegicus (775804 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Htr2c Serotonin 2c (5-HT2c) receptor (1134 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Htr2a Serotonin 2a (5-HT2a) receptor (3540 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Oryctolagus cuniculus (11301 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Htr2b Serotonin 2b (5-HT2b) receptor (321 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: YesOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Properties

Molecular Weight: 225.29Molecular Weight (Monoisotopic): 225.1365AlogP: 1.60#Rotatable Bonds: 5
Polar Surface Area: 53.71Molecular Species: BASEHBA: 4HBD: 1
#RO5 Violations: 0HBA (Lipinski): 4HBD (Lipinski): 2#RO5 Violations (Lipinski): 0
CX Acidic pKa: CX Basic pKa: 9.94CX LogP: 1.33CX LogD: -1.09
Aromatic Rings: 1Heavy Atoms: 16QED Weighted: 0.83Np Likeness Score: 0.24

References

1. Seggel MR, Yousif MY, Lyon RA, Titeler M, Roth BL, Suba EA, Glennon RA..  (1990)  A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors.,  33  (3): [PMID:2308135] [10.1021/jm00165a023]
2. Glennon RA, Young R, Benington F, Morin RD..  (1982)  Behavioral and serotonin receptor properties of 4-substituted derivatives of the hallucinogen 1-(2,5-dimethoxyphenyl)-2-aminopropane.,  25  (10): [PMID:7143352] [10.1021/jm00352a013]
3. Glennon RA..  (1987)  Central serotonin receptors as targets for drug research.,  30  (1): [PMID:3543362] [10.1021/jm00384a001]
4. Domelsmith LN, Eaton TA, Houk KN, Anderson GM, Glennon RA, Shulgin AT, Castagnoli N, Kollman PA..  (1981)  Photoelectron spectra of psychotropic drugs. 6. Relationships between the physical properties and pharmacological actions of amphetamine analogues.,  24  (12): [PMID:7310818] [10.1021/jm00144a009]
5. Peddi S, Roth BL, Glennon RA, Westkaemper RB..  (2003)  Ring substituted analogues of 5-aminomethyl-10,11-dihydro-dibenzo[a,d]cycloheptene (AMDH): potential modes of binding to the 5-HT(2A) receptor.,  13  (15): [PMID:12852967] [10.1016/s0960-894x(03)00504-3]
6. Glennon RA, Liebowitz SM, Anderson GM..  (1980)  Serotonin receptor affinities of psychoactive phenalkylamine analogues.,  23  (3): [PMID:7365744] [10.1021/jm00177a017]
7. Clare BW..  (1998)  The frontier orbital phase angles: novel QSAR descriptors for benzene derivatives, applied to phenylalkylamine hallucinogens.,  41  (20): [PMID:9748359] [10.1021/jm980144c]
8. Clare BW..  (1990)  Structure-activity correlations for psychotomimetics. 1. Phenylalkylamines: electronic, volume, and hydrophobicity parameters.,  33  (2): [PMID:2299636] [10.1021/jm00164a036]
9. Glennon RA, Raghupathi R, Bartyzel P, Teitler M, Leonhardt S..  (1992)  Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity.,  35  (4): [PMID:1542100] [10.1021/jm00082a014]
10. Runyon SP, Mosier PD, Roth BL, Glennon RA, Westkaemper RB..  (2008)  Potential modes of interaction of 9-aminomethyl-9,10-dihydroanthracene (AMDA) derivatives with the 5-HT2A receptor: a ligand structure-affinity relationship, receptor mutagenesis and receptor modeling investigation.,  51  (21): [PMID:18847250] [10.1021/jm800771x]
11. Kier LB, Hall LH..  (1977)  Structure-activity studies on hallucinogenic amphetamines using molecular connectivity.,  20  (12): [PMID:592329] [10.1021/jm00222a019]
12. Glennon RA, Liebowitz SM, Mack EC..  (1978)  Serotonin receptor binding affinities of several hallucinogenic phenylalkylamine and N,N-dimethyltryptamine analogues.,  21  (8): [PMID:278843] [10.1021/jm00206a022]
13. Glennon RA..  (2017)  The 2014 Philip S. Portoghese Medicinal Chemistry Lectureship: The "Phenylalkylaminome" with a Focus on Selected Drugs of Abuse.,  60  (7): [PMID:28244748] [10.1021/acs.jmedchem.7b00085]

Source