JAZL/ChemGist-CHON huggingface dataset:
Compound: Bohd
SMILES: O(c1c(cc(OC)c(c1)C)C(O)CN)C
InChIKey: WCURBUJUIMRCCJ-UHFFFAOYSA-N
Synonyms: Bohd, 4-Methyl-2,5-dimethoxy-beta-hydroxyphenethylamine, 29348-16-1, UNII-QX20VMP285, QX20VMP285, Benzenemethanol, alpha-(aminomethyl)-2,5-dimethoxy-4-methyl-, 2-(2,5-Dimethoxy-4-methylphenyl)-2-hydroxyethylamine, alpha-(Aminomethyl)-2,5-dimethoxy-4-methylbenzenemethanol, Benzyl alcohol, alpha-(aminomethyl)-2,5-dimethoxy-4-methyl-, BOHD (psychedelic), SCHEMBL20970925, SCHEMBL29543324, DTXSID70660352, Q4836199, 2-Amino-1-(2,5-dimethoxy-4-methylphenyl)ethan-1-ol, .ALPHA.-(AMINOMETHYL)-2,5-DIMETHOXY-4-METHYLBENZENEMETHANOL, BENZENEMETHANOL, .ALPHA.-(AMINOMETHYL)-2,5-DIMETHOXY-4-METHYL-, BENZYL ALCOHOL, .ALPHA.-(AMINOMETHYL)-2,5-DIMETHOXY-4-METHYL-
Theoretical properties:
molecular_formula: C11H17NO3
molecular_weight: 211.26 g/mol
exact_mass: 211.12084340 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 4
heavy_atom_count: 15
topological_polar_surface_area: 64.7 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
wikipedia: BOHD, also known as 4-methyl-2,5-dimethoxy-β-hydroxyphenethylamine or as β-hydroxy-2C-D, is a drug of the phenethylamine, 2C, and BOx families. It is the β-hydroxy derivative of 2C-D.
Compound: beta-Methoxymescaline
SMILES: O(c1c(OC)cc(C(OC)CN)cc1OC)C
InChIKey: GAKIJEPUVBHWCK-UHFFFAOYSA-N
Synonyms: beta-Methoxymescaline, 3,4,5,beta-Tetramethoxyphenethylamine, 98537-40-7, Benzeneethanamine, beta,3,4,5-tetramethoxy-, UNII-ZYL4Q2506P, ZYL4Q2506P, J961.027H, (+/-)-2-(3,4,5-Trimethoxyphenyl)-2-methoxyethylamine, Phenethylamine, beta,3,4,5-tetramethoxy-, BOM, BOM (psychedelic), 2-methoxy-2-(3,4,5-trimethoxyphenyl)ethanamine, .BETA.-METHOXYMESCALINE, SCHEMBL20970913, DTXSID30660353, AKOS015157590, 3,4,5,.BETA.-TETRAMETHOXYPHENETHYLAMINE, PHENETHYLAMINE, .BETA.,3,4,5-TETRAMETHOXY-, Q4836214, 2-Methoxy-2-(3,4,5-trimethoxyphenyl)ethan-1-amine, BENZENEETHANAMINE, .BETA.,3,4,5-TETRAMETHOXY-
Theoretical properties:
molecular_formula: C12H19NO4
molecular_weight: 241.28 g/mol
exact_mass: 241.13140809 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 6
heavy_atom_count: 17
topological_polar_surface_area: 62.9 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
wikipedia: BOM, also known as 3,4,5,β-tetramethoxyphenethylamine or as β-methoxymescaline, is a psychoactive drug of the phenethylamine, scaline, and BOx families related to mescaline. It is the β-methoxy derivative of mescaline.
Compound: Acylfulvene
SMILES: O=C1C=2C(=C(C)C3([C@]1(O)C)CC3)C=C(C2)C
InChIKey: HLAKJNQXUARACO-ZDUSSCGKSA-N
Synonyms: Acylfulvene, (-)-acylfulvene, Acylfulvene, (-)-, G4T2FA57Q6, DTXSID30327131, (5'R)-5'-hydroxy-2',5',7'-trimethylspiro[cyclopropane-1,6'-indene]-4'-one, (5'R)-5'-hydroxy-2',5',7'-trimethylspiro(cyclopropane-1,6'-indene)-4'-one, RefChem:915126, DTXCID20278244, 125392-76-9, Illudofulvene, UNII-G4T2FA57Q6, NSC633555, (6'R)-6'-Hydroxy-2',4',6'-trimethyl-6',7'-dihydrospiro(cyclopropane-1,5'-indene)-7'-one, (6'R)-6'-Hydroxy-2',4',6'-trimethylspiro(cyclopropane-1,5'-(5H)inden)-7'(6'H)-one, (R)-6'-Hydroxy-2',4',6'-trimethylspiro[cyclopropane-1,5'-inden]-7'(6'H)-one, Spiro(cyclopropane-1,5'-(5H)inden)-7'(6'H)-one, 6'-hydroxy-2',4',6'-trimethyl-, (R)-, Spiro[cyclopropane-1,5'-[5H]inden]-7'(6'H)-one, 6'-hydroxy-2',4',6'-trimethyl-, (6'R)-, (6'R)-6'-Hydroxy-2',4',6'-trimethylspiro[cyclopropane-1,5'-[5H]inden]-7'(6'H)-one; (6'R)-6'-Hydroxy-2',4',6'-trimethyl-6',7'-dihydrospiro[cyclopropane-1,5'-indene]-7'-one; (R)-6'-Hydroxy-2',4',6'-trimethyl-spiro[cyclopropane-1,5'-[5H]inden]-7'(6'H)-one; Acylfulvene; Illudofulvene, NSC-633555, (6'R)-6'-hydroxy-2',4',6'-trimethylspiro[cyclopropane-1,5'-inden]-7'(6'H)-one, CHEMBL121987, orb2944242, SCHEMBL17168188, SCHEMBL23854820, BDBM50410833, MFCD00904093, NCI60_011189, SY339379, Q4678004, (R)-6 inverted exclamation mark -Hydroxy-2 inverted exclamation mark ,4 inverted exclamation mark ,6 inverted exclamation mark -trimethylspiro[cyclopropane-1,5 inverted exclamation mark -inden]-7 inverted exclamation mark (6 inverted exclamation mark H)-one
Theoretical properties:
molecular_formula: C14H16O2
molecular_weight: 216.27 g/mol
exact_mass: 216.115029749 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 0
heavy_atom_count: 16
topological_polar_surface_area: 37.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
chembl: ACYLFULVENE is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Acylfulvene is a class of cytotoxic semi-synthetic derivatives of illudin, a natural product that can be extracted from the jack o'lantern mushroom (Omphalotus olearius).  One important acylfulvene, 6-hydroxymethylacylfulvene (irofulven), has been evaluated for the treatment of a wide assortment of cancers and tumors. It is thought that acylfulvene compounds kill cancer cells by DNA alkylation (see DNA methylation).
Compound: 33781-60-1
SMILES: O=C1C=2C(=C(C)C3(C1(O)C)CC3)C=C(C2)C
InChIKey: HLAKJNQXUARACO-UHFFFAOYSA-N
Synonyms: 33781-60-1, (+/-)-Acylfulvene, 5'-hydroxy-2',5',7'-trimethylspiro[cyclopropane-1,6'-indene]-4'-one, 652134-40-2, N-[(1,1-Dimethylethoxy)carbonyl]-L-?-glutamyl-L-cysteinyl-glycine Dimethyl Ester; N-[N-[N-[(1,1-dimethylethoxy)carbonyl]-L-?-glutamyl]-L-cysteinyl]-glycine Dimethyl Ester, Acylfulvene, (+/-)-, YG9RV5EMS6, Neuro_000281, SCHEMBL61769, AFA39276, IBA78160, MFCD28143178, MFCD34690498, 6'-Hydroxy-2',4',6'-trimethylspiro[cyclopropane-1,5'-inden]-7'(6'H)-one, SY339381, SY383300, 6'-Hydroxy-2',4',6'-trimethylspiro[cyclopropane-1,5'-[5H]inden]-7'(6'H)-one, Spiro[cyclopropane-1,5'-[5H]inden]-7'(6'H)-one, 6'-hydroxy-2',4',6'-trimethyl-, (S)-6 inverted exclamation mark -Hydroxy-2 inverted exclamation mark ,4 inverted exclamation mark ,6 inverted exclamation mark -trimethylspiro[cyclopropane-1,5 inverted exclamation mark -inden]-7 inverted exclamation mark (6 inverted exclamation mark H)-one, 6 inverted exclamation mark -Hydroxy-2 inverted exclamation mark ,4 inverted exclamation mark ,6 inverted exclamation mark -trimethylspiro[cyclopropane-1,5 inverted exclamation mark -inden]-7 inverted exclamation mark (6 inverted exclamation mark H)-one
Theoretical properties:
molecular_formula: C14H16O2
molecular_weight: 216.27 g/mol
exact_mass: 216.115029749 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 0
heavy_atom_count: 16
topological_polar_surface_area: 37.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
wikipedia: The insulin-like growth factor 1 (IGF-1) receptor is a protein found on the surface of human cells. It is a transmembrane receptor that is activated by a hormone called insulin-like growth factor 1 (IGF-1) and by a related hormone called IGF-2. It belongs to the large class of tyrosine kinase receptors.  This receptor mediates the effects of IGF-1, which is a polypeptide protein hormone similar in molecular structure to insulin. IGF-1 plays an important role in growth and continues to have anabolic effects in adults – meaning that it can induce hypertrophy of skeletal muscle and other target tissues. Mice lacking the IGF-1 receptor die late in development, and show a dramatic reduction in body mass. This testifies to the strong growth-promoting effect of this receptor.
Compound: Beta-D
SMILES: O(c1c(OC)cc(C(CN)([2H])[2H])cc1OC)C
InChIKey: RHCSKNNOAZULRK-APZFVMQVSA-N
Synonyms: Beta-D, UP9QBW4UM9, 1020518-89-1, RefChem:1079636, Mescaline, beta-dideutero, 3,4,5-Trimethoxy-beta-dideuterophenethylamine, UNII-UP9QBW4UM9, 2-(3,4,5-Trimethoxyphenyl)(2,2-2H2)ethan-1-amine, SCHEMBL20970961, DTXSID00660360, 2-(3,4,5-Trimethoxyphenyl)(2,2-2H2)ethanamine, Q4897180, 2-(3,4,5-Trimethoxyphenyl)(2,2-~2~H_2_)ethan-1-amine
Theoretical properties:
molecular_formula: C11H17NO3
molecular_weight: 213.27 g/mol
exact_mass: 213.13339690 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 5
heavy_atom_count: 15
topological_polar_surface_area: 53.7 Å²
isotope_atom_count: 2
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
chebi: A primary ammonium ion that is the conjugate acid of mescaline resulting from the protonation of the primary amino group; Major microspecies at pH 7.3.
wikipedia: Beta-D, or β-D, also known as 3,4,5-trimethoxy-β,β-dideuterophenethylamine or as β,β-dideuteromescaline, is a psychedelic drug of the scaline family related to mescaline. It is the isotopologue of mescaline in which the two hydrogen atoms at the β position have been replaced with the deuterium isotopes.
In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists β-D's dose as 200 to 400 mg orally in the case of the sulfate salt or 178 to 356 mg orally in the case of the hydrochloride salt and its duration as 12 hours. The onset ranged from 15 minutes to 1.5 hours. The drug produces hallucinogenic effects similarly to mescaline, with these effects of β-D having been thoroughly described. It is thought to be very similar or indistinguishable in terms of properties, effects, and metabolism compared to mescaline.
The chemical synthesis of β-D has been described. Other deuterated isotopologues of mescaline are also known, such as 4-D (4-trideuteromescaline) and α-D (alpha-D; α,α-dideuteromescaline), among others. α-D may be resistant to the oxidative deamination that is known to occur with mescaline, which may result in it being more potent than mescaline. However, α-D is not known to have been studied.
β-D was described by Shulgin in his book PiHKAL in 1991. It does not seem to be a controlled substance in Canada as of 2025.
Compound: 2,5-Dimethoxy-4-butylamphetamine
SMILES: O(c1c(cc(OC)c(c1)CCCC)CC(N)C)C
InChIKey: NGVDYAULSQKEGW-UHFFFAOYSA-N
Synonyms: 2,5-Dimethoxy-4-butylamphetamine, 63779-89-5, 6ARH6DPN4N, UNII-6ARH6DPN4N, Benzeneethanamine, 4-butyl-2,5-dimethoxy-alpha-methyl-, 4-BUTYL-2,5-DIMETHOXY-.ALPHA.-METHYLBENZENEETHANAMINE, BENZENEETHANAMINE, 4-BUTYL-2,5-DIMETHOXY-.ALPHA.-METHYL-, RefChem:82889, 4-BUTYL-2,5-DIMETHOXY-ALPHA-METHYLBENZENEETHANAMINE, (+-)-1-(2,5-DIMETHOXY-4-N-BUTYLPHENYL)-2-AMINOPROPANE, DOBU, 1-(4-BUTYL-2,5-DIMETHOXYPHENYL)PROPAN-2-AMINE, CHEMBL8214, alpha-Methyl-4-butyl-2,5-dimethoxyphenethylamine, (+/-)-1-(2,5-Dimethoxy-4-N-butylphenyl)-2-aminopropane, 1-(4-butyl-2,5-dimethoxy-phenyl)propan-2-amine, SCHEMBL713029, DTXSID90434976, 4-butyl-2,5-dimethoxyamphetamine, NCA77989, BDBM50005261, PDSP1_001368, PDSP2_001352, DB-309521, NS00017750, Q4596790, 2-(4-Butyl-2,5-dimethoxy-phenyl)-1-methyl-ethylamine
Theoretical properties:
molecular_formula: C15H25NO2
molecular_weight: 251.36 g/mol
exact_mass: 251.188529040 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 7
heavy_atom_count: 18
topological_polar_surface_area: 44.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
chembl: Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: 2,5-Dimethoxy-4-butylamphetamine (DOBU) is a psychedelic drug of the phenethylamine, amphetamine, and DOx families related to DOM. It is the derivative of DOM in which the methyl group at the 4 position has been replaced with a butyl group. The drug is taken orally.
It acts as a serotonin receptor agonist, including of the serotonin 5-HT2A receptor. The drug produces psychedelic-like effects in animals.
DOBU was first described in the literature by Alexander Shulgin in 1970. Subsequently, it was described in greater detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).
Compound: CYCLOHEPTANE
SMILES: C1CCCCCC1
InChIKey: DMEGYFMYUHOHGS-UHFFFAOYSA-N
Synonyms: CYCLOHEPTANE, 291-64-5, Suberane, Heptamethylene, UNII-VTZ53P34JA, VTZ53P34JA, HSDB 59, NSC 5164, NSC-5164, EINECS 206-030-2, DTXSID0074269, RefChem:5717, DTXCID1037931, 206-030-2, MFCD00004147, cycloheptan, UN2241, Cycloheptane, 98%, SCHEMBL892, SCHEMBL2315, SCHEMBL8198, HEPTAMETHYLENE [HSDB], SCHEMBL101586, SCHEMBL113561, SCHEMBL132497, SCHEMBL333890, CHEMBL453194, SCHEMBL1672487, SCHEMBL1723224, SCHEMBL2232677, SCHEMBL2466994, SCHEMBL3029005, SCHEMBL5397984, SCHEMBL7689031, SCHEMBL7689970, SCHEMBL7689983, SCHEMBL7694325, SCHEMBL7695201, SCHEMBL7695861, SCHEMBL7696851, SCHEMBL7697307, SCHEMBL7697373, NSC5164, SBB060406, AKOS015903170, DB-047533, Cycloheptane [UN2241]  [Flammable liquid], NS00042145, ST51046592, D89252, Q423957, InChI=1/C7H14/c1-2-4-6-7-5-3-1/h1-7H
Theoretical properties:
molecular_formula: C7H14
molecular_weight: 98.19 g/mol
exact_mass: 98.109550447 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 0
rotatable_bond_count: 0
heavy_atom_count: 7
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Colorless liquid
color: Colorless liquid
boiling_point: 245.3 °F at 760 mmHg (USCG, 1999)
melting_point: 10.4 °F (USCG, 1999)
density: 0.811 (USCG, 1999) - Less dense than water; will float
solubility: In water, 30 mg/L at 25 °C
flash_point: 43 °F (USCG, 1999)
vapor_pressure: 44 mmHg (USCG, 1999)
Descriptions:
chembl: CYCLOHEPTANE is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Cycloheptane, also known as suberane, is an organic compound, which belongs to the group of cycloalkanes. The compound can occur in different conformers.
Compound: 3-NITROBENZOIC ACID
SMILES: O=[N+]([O-])c1cc(C(=O)O)ccc1
InChIKey: AFPHTEQTJZKQAQ-UHFFFAOYSA-N
Synonyms: 3-NITROBENZOIC ACID, 121-92-6, m-Nitrobenzoic acid, Benzoic acid, 3-nitro-, Benzoic acid, m-nitro-, m-Nitrobenzenecarboxylic acid, Metanitrobenzoic acid, meta-Nitrobenzoic acid, M-CARBOXYNITROBENZENE, DTXSID0025737, NSC-9801, H318ZW7612, DTXCID605737, RefChem:95028, 204-508-5, 3-Nitro-benzoic acid, MFCD00007251, CAS-121-92-6, CCRIS 2335, HSDB 6028, NSC 9801, EINECS 204-508-5, BRN 0908644, AI3-09015, UNII-H318ZW7612, 3-nitro benzoic acid, WLN: WNR CVQ, 3-NITROBENZOICACID, SCHEMBL132618, CHEMBL274839, SCHEMBL2170995, SCHEMBL2204741, SCHEMBL3049742, SCHEMBL4827704, SCHEMBL7406647, SCHEMBL17347335, SCHEMBL29490968, NSC9801, CHEBI:231494, 3-NITROBENZOIC ACID [HSDB], HY-Y1313, STR01384, Tox21_201238, Tox21_303250, SBB058220, STK301724, 3-Nitrobenzoic acid, puriss., 99%, AKOS000119012, AC-2834, CS-W020596, EBC-151044, FN70301, PS-5143, NCGC00091521-01, NCGC00091521-02, NCGC00091521-03, NCGC00257168-01, NCGC00258790-01, 3-Nitrobenzoic acid, ReagentPlus(R), 99%, N0154, NS00019769, ST45061531, EN300-18006, BENZOIC ACID,3-NITRO  MFC7 H5 N1 O4, 3-Nitrobenzoic acid, purum, >=98.0% (HPLC), F209438, 3-Nitrobenzoic acid, Vetec(TM) reagent grade, 98%, Q4634183, Z57127479, F2191-0133, InChI=1/C7H5NO4/c9-7(10)5-2-1-3-6(4-5)8(11)12/h1-4H,(H,9,10, 27178-83-2
Theoretical properties:
molecular_formula: C7H5NO4
molecular_weight: 167.12 g/mol
exact_mass: 167.02185764 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 1
heavy_atom_count: 12
topological_polar_surface_area: 83.1 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Monoclinic leaflets or prisms
color: Monoclinic leaflets or prisms
melting_point: 284 to 288 °F (NTP, 1992)
density: 1.494 at 68 °F (NTP, 1992) - Denser than water; will sink
solubility: less than 0.1 mg/mL at 64 °F (NTP, 1992)
vapor_pressure: 0.0000371 [mmHg]
Descriptions:
pubchem: 3-nitrobenzoic acid is a nitrobenzoic acid having the nitro group at the 3-position. It is a conjugate acid of a 3-nitrobenzoate.
chebi: A nitrobenzoic acid having the nitro group at the 3-position.
chembl: Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: 3-Nitrobenzoic acid is an organic compound with the formula C6H4(NO2)CO2H. It is an aromatic compound and under standard conditions, it is an off-white solid. The two substituents are in a meta position with respect to each other, giving the alternative name of m-nitrobenzoic acid. This compound can be useful as it is a precursor to 3-aminobenzoic acid, which is used to prepare some dyes.
Compound: 2,5-Dimethoxy-4-propylamphetamine
SMILES: O(c1c(cc(OC)c(c1)CCC)CC(N)C)C
InChIKey: UEEAUFJYLUJWQJ-UHFFFAOYSA-N
Synonyms: 2,5-Dimethoxy-4-propylamphetamine, UNII-L3P287BI9W, J273.474E, L3P287BI9W, 63779-88-4, Benzeneethanamine, 2,5-dimethoxy-alpha-methyl-4-propyl-, DTXSID40337347, BENZENEETHANAMINE, 2,5-DIMETHOXY-.ALPHA.-METHYL-4-PROPYL-, RefChem:82903, DTXCID30288435, (+-)-1-(2,5-DIMETHOXY-4-N-PROPYLPHENYL)-2-AMINOPROPANE, UEEAUFJYLUJWQJ-UHFFFAOYSA-N, DOPR, CHEMBL8569, (+/-)-1-(2,5-Dimethoxy-4-N-propylphenyl)-2-aminopropane, 1-(2,5-dimethoxy-4-propylphenyl)propan-2-amine, DOPR (PSYCHEDELIC), 2,5-Dimethoxy-alpha-methyl-4-propylbenzeneethaneamine, SCHEMBL5470316, BDBM50005249, PDSP1_000459, PDSP2_000457, DB-292306, 1-(2,5-Dimethoxy-4-propylphenyl)-2-propanamine #, Q4596792, 2-(2,5-Dimethoxy-4-propyl-phenyl)-1-methyl-ethylamine, 2-(2,5-Dimethoxy-4-propyl-phenyl)-1-methyl-ethylamine(DOPR)
Theoretical properties:
molecular_formula: C14H23NO2
molecular_weight: 237.34 g/mol
exact_mass: 237.172878976 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 6
heavy_atom_count: 17
topological_polar_surface_area: 44.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
chembl: Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: 2,5-Dimethoxy-4-propylamphetamine (DOPR) is a psychedelic drug of the phenethylamine, amphetamine, and DOx families related to DOM. It is the derivative of DOM in which the methyl group at the 4 position has been replaced with a propyl group. The drug is taken orally.
The drug acts as a serotonin receptor agonist, including of the serotonin 5-HT2A receptor. It produces psychedelic-like effects in animals.
DOPR was first described in the literature by Alexander Shulgin in 1970. Subsequently, it was described in greater detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).
Compound: 63779-90-8
SMILES: O(c1c(cc(OC)c(c1)CCCCC)CC(N)C)C
InChIKey: VLJORLCVOAUUKM-UHFFFAOYSA-N
Synonyms: 63779-90-8, DOAM, 2,5-Dimethoxy-4-pentylamphetamine, 2,5-Dimethoxy-4-amylamphetamine, 1-(2,5-DIMETHOXY-4-PENTYLPHENYL)PROPAN-2-AMINE, N80EWL36CB, UNII-N80EWL36CB, alpha-Methyl-4-amyl-2,5-dimethoxyphenethylamine, CHEMBL161416, orb2814362, SCHEMBL5305816, SCHEMBL29539016, DTXSID50482958, BDBM674373, US20240166618, Compound 23, US20240166618, Compound 29, CS-0083652, NS00018002, 1-(2,5-dimethoxy-4-pentyl-phenyl)propan-2-amine, Q4596788, 2,5-Dimethoxy-I+/--methyl-4-pentylbenzeneethanamine, Benzeneethanamine, 2,5-dimethoxy-alpha-methyl-4-pentyl-, BENZENEETHANAMINE, 2,5-DIMETHOXY-.ALPHA.-METHYL-4-PENTYL-
Theoretical properties:
molecular_formula: C16H27NO2
molecular_weight: 265.39 g/mol
exact_mass: 265.204179104 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 8
heavy_atom_count: 19
topological_polar_surface_area: 44.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
chembl: Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: 4-Substituted-2,5-dimethoxyamphetamines (DOx) is a chemical class of substituted amphetamine derivatives featuring methoxy groups at the 2- and 5- positions of the phenyl ring, and a substituent such as alkyl or halogen at the 4- position of the phenyl ring. They are 4-substituted derivatives of 2,5-dimethoxyamphetamine (2,5-DMA, DOH) and are structurally related to the naturally occurring phenethylamine psychedelic mescaline.
The most well-known DOx drugs are DOM, DOI, DOB, DOET, and DOC. DOI is widely used in scientific research. DOM has been used as a recreational drug, while DOET was an experimental pharmaceutical drug.
Most compounds of this class are potent and long-lasting psychedelic drugs, and act as selective 5-HT2A, 5-HT2B, and 5-HT2C receptor agonists. A few bulkier derivatives such as DOAM have similarly high affinity for 5-HT2 receptors but have reduced efficacy and potency as psychedelics.
DOI has been found to have extraordinarily potent anti-inflammatory effects. These properties are not shared by all other related drugs and appear to be mediated by functionally selective serotonin 5-HT2A receptor activation. The anti-inflammatory effects of DOI and related drugs may have medical applications.
Compound: 2,3-Dimethoxyamphetamine
SMILES: O(c1c(OC)cccc1CC(N)C)C
InChIKey: DHLWJXGSZDJWKK-UHFFFAOYSA-N
Synonyms: 2,3-Dimethoxyamphetamine, Benzeneethanamine, 2,3-dimethoxy-alpha-methyl-, 15402-81-0, P5Z6ZU6N7S, CHEMBL280855, Benzeneethanamine,2,3-dimethoxy-.alpha.-methyl-, 1-(2,3-dimethoxyphenyl)propan-2-amine, UNII-P5Z6ZU6N7S, SCHEMBL729393, DTXSID20934898, DHLWJXGSZDJWKK-UHFFFAOYSA-N, BDBM50091080, AKOS000152288, 2,3-DIMETHOXYPHENYLISOPROPYLAMINE, 1-(2,3-Dimethoxyphenyl)-2-propanamine #, Q2506164, (+/-)2-(2,3-Dimethoxy-phenyl)-1-methyl-ethylamine, PHENETHYLAMINE, 2,3-DIMETHOXY-.ALPHA.-METHYL-, BENZENEETHANAMINE, 2,3-DIMETHOXY-.ALPHA.-METHYL-
Theoretical properties:
molecular_formula: C11H17NO2
molecular_weight: 195.26 g/mol
exact_mass: 195.125928785 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 4
heavy_atom_count: 14
topological_polar_surface_area: 44.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
chembl: Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: 2,3-Dimethoxyamphetamine (2,3-DMA), also known as DMA-2, is a drug of the phenethylamine and amphetamine families. It is one of the positional isomers of dimethoxyamphetamine.
2,3-DMA does not appear to have been tested in humans.
The drug showed weak affinity for serotonin receptors in rat stomach fundus strips (A2 = 2,880 nM). In a subsequent study, 2,3-DMA showed very low affinity for the serotonin 5-HT2A and 5-HT2C receptors (Ki = 4,280 nM and >10,000 nM, respectively). It did not show activity as a norepinephrine releasing agent in vitro. The drug is behaviorally active in mice. 2,3-DMA did not substitute for DOM in rodent drug discrimination tests. However, it did partially substitute for 5-MeO-DMT in these tests. As with DOM, the drug did not substitute for dextroamphetamine in drug discrimination tests. It produced behavioral disruption at higher doses.
The chemical synthesis of 2,3-DMA has been described.
2,3-DMA was first described in the scientific literature by F. Benington and colleagues by 1968. Alexander Shulgin first described 2,3-DMA in 1969 but had not yet synthesized it and did not report its effects.