JAZL/ChemGist-CHON huggingface dataset:
Compound: RU28362
SMILES: O=C1C=C2C(=C[C@H]3[C@H]4[C@]([C@](O)(C#CC)CC4)(C)C[C@@H]([C@@H]3[C@@]2(C)C=C1)O)C
InChIKey: UFZKDKHLKHEFGA-ZFTCBNFESA-N
Synonyms: RU28362, 74915-64-3, RU-28362, RU 28362, 11,17-dihydroxy-6-methyl-17-(1-propynyl)androsta-1,4,6-triene-3-one, (8S,9S,10R,11S,13S,14S,17S)-11,17-dihydroxy-6,10,13-trimethyl-17-prop-1-ynyl-9,11,12,14,15,16-hexahydro-8H-cyclopenta[a]phenanthren-3-one, VH397CN9SV, RU 362, DTXSID101027141, RU362, RU28362-6, Androsta-1,4,6-trien-3-one, 11,17-dihydroxy-6-methyl-17-(1-propynyl)-, (11beta,17beta)-, (8S,9S,10R,11S,13S,14S,17S)-11,17-dihydroxy-6,10,13-trimethyl-17-prop-1-ynyl-9,11,12,14,15,16-hexahydro-8H-cyclopenta(a)phenanthren-3-one, RefChem:930948, DTXCID801511381, RU-362, UNII-VH397CN9SV, GTPL3445, orb1699445, SCHEMBL10599789, AKOS040749370, DA-57564, HY-121859, CS-0083558, Q7277962, (11.BETA.,17.BETA.)-11,17-DIHYDROXY-6-METHYL-17-(1-PROPYNYL)ANDROSTA-1,4,6-TRIEN-3-ONE, ANDROSTA-1,4,6-TRIEN-3-ONE, 11,17-DIHYDROXY-6-METHYL-17-(1-PROPYNYL)-, (11.BETA.,17.BETA.)-
Theoretical properties:
molecular_formula: C23H28O3
molecular_weight: 352.5 g/mol
exact_mass: 352.20384475 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 1
heavy_atom_count: 26
topological_polar_surface_area: 57.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
wikipedia: RU-28362 is a synthetic androstane glucocorticoid that was developed by Roussel Uclaf. It is a selective agonist of the glucocorticoid receptor (corticoid type II receptor), but not of the mineralocorticoid receptor (corticoid type I receptor).
A similar compound is dexamethasone that also selectively binds to the glucocorticoid receptor with high affinity. This is in contrast to the natural steroid hormones cortisol or corticosterone, which bind to both of the corticosteroid receptors, though they bind to the mineralocorticoid receptor with greater affinity.
SMILES: O=c1oc2c(c(OC/C=C(/CCC=C(C)C)\C)c3ccoc3c2)cc1
InChIKey: DBMJZOMNXBSRED-OQLLNIDSSA-N
Theoretical properties:
Physical properties:
Descriptions:
chembl: BERGAMOTTIN is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
Compound: Diproqualone
SMILES: O=c1n(c(nc2c1cccc2)C)CC(O)CO
InChIKey: NTGLQWGMESPVBV-UHFFFAOYSA-N
Synonyms: Diproqualone, 36518-02-2, Diprocualona, Diproqualonum, QY7HLH8V4L, RefChem:1083818, 253-081-1, 3-(2,3-dihydroxypropyl)-2-methylquinazolin-4-one, Diproqualone, (+)-, L2Y2CV3EW7, 3-(2,3-Dihydroxypropyl)-2-methyl-3,4-dihydroquinazolin-4-one, 3-(2,3-Dihydroxypropyl)-2-methyl-4(3H)-quinazolinone, 46800-89-9, 4(3H)-Quinazolinone, 3-(2,3-dihydroxypropyl)-2-methyl-, (+)-, Diproqualone [INN:DCF], UNII-QY7HLH8V4L, Diproqualonum [INN-Latin], Diprocualona [INN-Spanish], Diproqualon, 3-(2,3-dihydroxypropyl)-2-methylquinazolin-4(3h)-one, EINECS 253-081-1, DIPROQUALONE [INN], UNII-L2Y2CV3EW7, 52GGM7X5IG, DIPROQUALONE [MART.], DIPROQUALONE [WHO-DD], DIPROQUALONE, (-)-, orb2282977, SCHEMBL1266290, CHEMBL2106200, 4(3H)-Quinazolinone, 3-(2,3-dihydroxypropyl)-2-methyl-, DTXSID30865821, NTGLQWGMESPVBV-UHFFFAOYSA-N, LBA51802, MFCD00864326, HY-119404, CS-0068090, NS00057948, 3-(2,3-dihydroxypropyl)-2-methyl-quinazolin-4-one, Q5280078, 4(3H)-QUINAZOLINONE, 3-(2,3-DIHYDROXYPROPYL)-2-METHYL-, (-)-, 4(3H)-Quinazolinone, 3-(2,3-dihydroxypropyl)-2-methyl-; 3-(2,3-Dihydroxypropyl)-2-methyl-4(3H)-quinazolinone; Diproqualone; 3-(2,3-Dihydroxypropyl)-2-methylquinazolin-4-one
Theoretical properties:
molecular_formula: C12H14N2O3
molecular_weight: 234.25 g/mol
exact_mass: 234.10044231 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 3
heavy_atom_count: 17
topological_polar_surface_area: 73.1 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
chembl: DIPROQUALONE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.
wikipedia: Diproqualone is a quinazolinone class GABAergic and is an analogue of methaqualone developed in the late 1950s by a team at Nogentaise de Produits Chimique. It was marketed primarily in France and some other European countries. It has sedative, anxiolytic, antihistamine and analgesic properties, resulting from its agonist activity at the β subtype of the GABAa receptor, antagonist activity at all histamine receptors, inhibition of the
cyclooxygenase-1 enzyme, and possibly its agonist activity at both the sigma-1 receptor and sigma-2 receptor (the function of these receptors and their clinical relevance has not yet been determined). Diproqualone is used primarily for treating inflammatory pain associated with osteoarthritis and rheumatoid arthritis and more rarely, for treating insomnia, anxiety and neuralgia.
Diproqualone is the only analogue of methaqualone that is still in widespread clinical use, due to its useful anti-inflammatory and analgesic effects in addition to the sedative and anxiolytic actions common to other drugs of this class. There are still some concerns about the potential of diproqualone for abuse and overdose. So, it is not sold as a pure drug but only as the camphosulfonate salt in combination mixtures with other medicines such as ethenzamide.
Compound: Ketazocine
SMILES: O=C1c2c(cc(O)cc2)[C@@]3(CCN([C@H]1[C@@H]3C)CC4CC4)C
InChIKey: HQBZLVPZOGIAIQ-SDDDUWNISA-N
Synonyms: Ketazocine, Ketazocina, Ketazocinum, Win 34,276, WIN-34276, 6IO4IG518S, 3-(Cyclopropylmethyl)-3,4,5,6-tetrahydro-8-hydroxy-6,11-dimethyl-2,6-methano-3-benzazocin-1(2H)-one, DTXSID10897529, RefChem:151128, DTXCID301326884, 36292-69-0, (1R,9S,13R)-10-(cyclopropylmethyl)-4-hydroxy-1,13-dimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-8-one, (2R*,6S*,11S*)-3-(Cyclopropylmethyl)-3,4,5,6-tetrahydro-8-hydroxy-6,11-dimethyl-2,6-methano-3-benzazocin-1(2H)-one, Ketazocine [USAN:INN], Ketazocinum [INN-Latin], Ketazocina [INN-Spanish], UNII-6IO4IG518S, KETAZOCINE [INN], KETAZOCINE [USAN], SCHEMBL121212, CHEMBL2107292, BDBM50027366, (+)-3-(cyclopropylmethyl)-8-keto-5-(eq)-9-(ax)-dimethyl-6,7-benzomorphan, AKOS040746949, AC-24848, Q6395335, 2,6-METHANO-3-BENZAZOCIN-1(2H)-ONE, 3-(CYCLOPROPYLMETHYL)-3,4,5,6-TETRAHYDRO-8-HYDROXY-6,11-DIMETHYL-, (2.ALPHA.,6.ALPHA.,11S*)-, 2,6-Methano-3-benzazocin-1(2H)-one, 3-(cyclopropylmethyl)-3,4,5,6-tetrahydro-8-hydroxy-6,11-dimethyl-, (2alpha,6alpha,11S*)-
Theoretical properties:
molecular_formula: C18H23NO2
molecular_weight: 285.4 g/mol
exact_mass: 285.172878976 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 2
heavy_atom_count: 21
topological_polar_surface_area: 40.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
chembl: KETAZOCINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.
wikipedia: Ketazocine (INN), also known as ketocyclazocine, is a benzomorphan derivative used in opioid receptor research. Ketazocine, for which the receptor is named, is an exogenous opioid that binds to the κ opioid receptor.
Activation of this receptor is known to cause sleepiness, a decrease in pain sensation and (potentially) dysphoria, paranoia, and hallucinations. It also causes an increase in urine production because it inhibits the release of vasopressin.
Unlike other opioids, substances that only bind to the κ receptor theoretically do not depress the respiratory system.
The crystal structure of ketazocine was determined in 1983.
Compound: 3,4-Methylenedioxyphentermine
SMILES: O1c2c(ccc(c2)CC(N)(C)C)OC1
InChIKey: OIZBHKBNZXRXSM-UHFFFAOYSA-N
Synonyms: 3,4-Methylenedioxyphentermine, WF9K2PM8J8, 1-(2H-1,3-BENZODIOXOL-5-YL)-2-METHYLPROPAN-2-AMINE, alpha,alpha-dimethyl-3,4-methylenedioxyphenethylamine, DTXSID90515395, alpha,alpha-Dimethyl-1,3-benzodioxole-5-ethanamine, .ALPHA.,.ALPHA.-DIMETHYL-1,3-BENZODIOXOLE-5-ETHANAMINE, .ALPHA.,.ALPHA.-DIMETHYL-3,4-METHYLENEDIOXYPHENETHYLAMINE, RefChem:91263, DTXCID40466202, OIZBHKBNZXRXSM-UHFFFAOYSA-N, 39235-63-7, MDPH, UNII-WF9K2PM8J8, 1-(1,3-dioxaindan-5-yl)-2-methylpropan-2-amine, Methylenedioxyphentermine, 1,3-BENZODIOXOLE-5-ETHANAMINE, A,A-DIMETHYL-, CHEMBL126226, SCHEMBL9361284, SCHEMBL29543494, AKOS006311753, AB54594, EN300-1996327, Q6823993, 1,1-dimethyl-2-(3,4-methylenedioxyphenyl)ethylamine
Theoretical properties:
molecular_formula: C11H15NO2
molecular_weight: 193.24 g/mol
exact_mass: 193.110278721 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 2
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: MDPH, also known as 3,4-methylenedioxyphentermine or as α-methyl-MDA, is a psychoactive drug of the amphetamine family. MDPH was first synthesized by Alexander Shulgin. Very little data exists about the pharmacological properties, metabolism, and toxicity of MDPH.
Compound: 3C-BZ
SMILES: O(c1c(OC)cc(CC(N)C)cc1OC)Cc2ccccc2
InChIKey: IQKPLBJGFPDASR-UHFFFAOYSA-N
Synonyms: 3C-BZ, FH79WY8EA2, 147947-26-0, 4-benzyloxy-3,5-dimethoxyamphetamine, 3,5-Dimethoxy-alpha-methyl-4-(phenylmethoxy)benzeneethanamine, Benzeneethanamine, 3,5-dimethoxy-alpha-methyl-4-(phenylmethoxy)-, 3,5-DIMETHOXY-.ALPHA.-METHYL-4-(PHENYLMETHOXY)BENZENEETHANAMINE, BENZENEETHANAMINE, 3,5-DIMETHOXY-.ALPHA.-METHYL-4-(PHENYLMETHOXY)-, RefChem:198418, UNII-FH79WY8EA2, CHEMBL127871, SCHEMBL5308499, DTXSID20658385, 3,5-dimethoxy-4-benzyloxyamphetamine, Q4636224, 1-[4-(Benzyloxy)-3,5-dimethoxyphenyl]-2-propanamine, 1-[4-(Benzyloxy)-3,5-dimethoxyphenyl]propan-2-amine
Theoretical properties:
molecular_formula: C18H23NO3
molecular_weight: 301.4 g/mol
exact_mass: 301.16779360 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 7
heavy_atom_count: 22
topological_polar_surface_area: 53.7 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: 3C-BZ, also known as 4-benzyloxy-3,5-dimethoxyamphetamine or as α-methylbenzscaline (3C-benzscaline), is a psychedelic drug of the phenethylamine, amphetamine, and 3C families related to 3,4,5-trimethoxyamphetamine (TMA). It is the amphetamine (3C) analogue of benzscaline. The drug was first synthesized by Alexander Shulgin and described in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).
Compound: 3,4-Methylenedioxy-N-propylamphetamine
SMILES: O1c2c(ccc(c2)CC(NCCC)C)OC1
InChIKey: LBXMQBTXOLBCCA-UHFFFAOYSA-N
Synonyms: 3,4-Methylenedioxy-N-propylamphetamine, 3,4-Methylenedioxypropylamphetamine, B4W69BKX3L, 74698-36-5, 3,4-MDPA, alpha-methyl-N-propyl-1,3-benzodioxole-5-ethanamine, (1-(2H-1,3-Benzodioxol-5-yl)propan-2-yl)(propyl)amine, DTXSID50339877, 1,3-Benzodioxole-5-ethanamine, alpha-methyl-n-propyl-, N-(1-(1,3-Benzodioxol-5-yl)propan-2-yl)propan-1-amine, .ALPHA.-METHYL-N-PROPYL-1,3-BENZODIOXOLE-5-ETHANAMINE, 1,3-BENZODIOXOLE-5-ETHANAMINE, .ALPHA.-METHYL-N-PROPYL-, RefChem:486411, DTXCID90890790, MDPR, UNII-B4W69BKX3L, CHEMBL197038, SCHEMBL2418816, SCHEMBL29633088, LBXMQBTXOLBCCA-UHFFFAOYSA-N, N-Propyl-3,4-methylenedioxyamphetamine, PD048328, NS00003844, Q4634079, N-[1-(2H-1,3-Benzodioxol-5-yl)propan-2-yl]propan-1-amine, N-[2-(1,3-Benzodioxol-5-yl)-1-methylethyl]-1-propanamine #
Theoretical properties:
molecular_formula: C13H19NO2
molecular_weight: 221.29 g/mol
exact_mass: 221.141578849 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 5
heavy_atom_count: 16
topological_polar_surface_area: 30.5 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: MDPR, also known as 3,4-methylenedioxy-N-propylamphetamine or as N-propyl-MDA, is a lesser-known psychoactive drug and a substituted amphetamine.
Compound: MDPL
SMILES: O1c2c(ccc(c2)CC(NCC#C)C)OC1
InChIKey: LRYUTPIBTLEDJJ-UHFFFAOYSA-N
Synonyms: MDPL, TK2WH78T88, 74698-46-7, UNII-TK2WH78T88, 3,4-Methylenedioxy-N-propargylamphetamine, (1-(2H-1,3-Benzodioxol-5-yl)propan-2-yl)(prop-2-yn-1-yl)amine, 1,3-Benzodioxole-5-ethanamine, alpha-methyl-N-2-propynyl-, alpha-Methyl-N-2-propyn-1-yl-1,3-benzodioxole-5-ethanamine, Methylenedioxypropargylamphetamine, SCHEMBL5471018, SCHEMBL30183328, DTXSID70660372, Q282316, N-[1-(1,3-Benzodioxol-5-yl)-2-propanyl]-2-propyn-1-amine, N-[1-(2H-1,3-Benzodioxol-5-yl)propan-2-yl]prop-2-yn-1-amine, .ALPHA.-METHYL-N-2-PROPYN-1-YL-1,3-BENZODIOXOLE-5-ETHANAMINE, 1,3-BENZODIOXOLE-5-ETHANAMINE, .ALPHA.-METHYL-N-2-PROPYNYL-
Theoretical properties:
molecular_formula: C13H15NO2
molecular_weight: 217.26 g/mol
exact_mass: 217.110278721 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 4
heavy_atom_count: 16
topological_polar_surface_area: 30.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
wikipedia: MDPL, also known as 3,4-methylenedioxy-N-propargylamphetamine or as N-propargyl-MDA, is a lesser-known drug and a substituted amphetamine.
Compound: (4R,5S,8R,9R,11S,12S,13R,18S)-5,11-Dihydroxy-9,16-dimethyl-10-oxo-8-(6-oxopyran-3-yl)-15,17,20-trioxahexacyclo[14.3.1.114,18.01,13.04,12.05,9]henicosane-13-carbaldehyde
SMILES: O=c1occ([C@@H]2[C@]3(C(=O)[C@@H](O)[C@@H]4[C@]5(C=O)C6(OC7(O[C@H](C6)CC5O7)C)CC[C@H]4[C@@]3(O)CC2)C)cc1
InChIKey: PHOLEJIIASOWOL-SQBSQXRJSA-N
Synonyms: (4R,5S,8R,9R,11S,12S,13R,18S)-5,11-Dihydroxy-9,16-dimethyl-10-oxo-8-(6-oxopyran-3-yl)-15,17,20-trioxahexacyclo[14.3.1.114,18.01,13.04,12.05,9]henicosane-13-carbaldehyde, Q5209119
Theoretical properties:
molecular_formula: C26H30O9
molecular_weight: 486.5 g/mol
exact_mass: 486.18898253 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 9
rotatable_bond_count: 2
heavy_atom_count: 35
topological_polar_surface_area: 129 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
Compound: Daigremontianin
SMILES: O=c1occ([C@@H]2[C@]3(C(=O)[C@@H](O)[C@@H]4[C@]5(C=O)[C@]6(OC7(O[C@H](C6)C[C@H]5O7)C)CC[C@H]4[C@@]3(O)CC2)C)cc1
InChIKey: PHOLEJIIASOWOL-LGELPWFGSA-N
Synonyms: Daigremontianin, N5SG3A9FLM, DTXSID40897532, (1S,4R,5S,8R,9R,11S,12S,13R,14R,18S)-5,11-dihydroxy-9,16-dimethyl-10-oxo-8-(6-oxopyran-3-yl)-15,17,20-trioxahexacyclo[14.3.1.114,18.01,13.04,12.05,9]henicosane-13-carbaldehyde, Bufa-20,22-dienolide, 1,3,5-(ethylidynetris(oxy))-11,14-dihydroxy-12,19-dioxo-, (1beta(R),3beta,5beta,11alpha)-, (1S,4R,5S,8R,9R,11S,12S,13R,14R,18S)-5,11-dihydroxy-9,16-dimethyl-10-oxo-8-(6-oxopyran-3-yl)-15,17,20-trioxahexacyclo(14.3.1.114,18.01,13.04,12.05,9)henicosane-13-carbaldehyde, RefChem:130765, DTXCID701326886, (1S,4R,5S,8R,9R,11S,12S,13R,14R,16R,18S)-5,11-dihydroxy-9,16-dimethyl-10-oxo-8-(6-oxopyran-3-yl)-15,17,20-trioxahexacyclo(14.3.1.114,18.01,13.04,12.05,9)henicosane-13-carbaldehyde, UNII-N5SG3A9FLM, SCHEMBL1533540, (1S,4R,5S,8R,9R,11S,12S,13R,14R,18S)-5,11-Dihydroxy-9,16-dimethyl-10-oxo-8-(2-oxo-2H-pyran-5-yl)-15,17,20-trioxahexacyclo[14.3.1.1~14,18~.0~1,13~.0~4,12~.0~5,9~]henicosane-13-carbaldehyde
Theoretical properties:
molecular_formula: C26H30O9
molecular_weight: 486.5 g/mol
exact_mass: 486.18898253 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 9
rotatable_bond_count: 2
heavy_atom_count: 35
topological_polar_surface_area: 129 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
wikipedia: Daigremontianin is a bufadienolide. Bufadienolides are steroids and cardiac glycoside aglycones (meaning that they bind with carbohydrates to form cardiac glycosides) that are similar to cardenolides, differing only in the structure of the C-17 substituent on the D ring. This chemical has been found to be toxic in experiments on mice. It is one of five bufadienolides that have been isolated from Kalanchoe daigremontiana.
Compound: EDMA
SMILES: O1c2c(OCC1)ccc(c2)CC(NC)C
InChIKey: UJKWLAZYSLJTKA-UHFFFAOYSA-N
Synonyms: EDMA, Ethylenedioxymethylamphetamine, UJ7UU2C6E6, 133787-66-3, DTXSID501027143, RefChem:1084047, DTXCID901511384, (+/-)-Edma, 3,4-ethylenedioxy-N-methylamphetamine, UNII-UJ7UU2C6E6, CHEMBL3603954, 1-(2,3-dihydro-1,4-benzodioxin-6-yl)-N-methylpropan-2-amine, 1,4-Benzodioxin-6-ethanamine, 2,3-dihydro-N,alpha-dimethyl-, SCHEMBL2780037, SCHEMBL29565154, UJKWLAZYSLJTKA-UHFFFAOYSA-N, BDBM50114072, PD046896, NS00017632, Q5322853, 1,4-BENZODIOXIN-6-ETHANAMINE, 2,3-DIHYDRO-N,.ALPHA.-DIMETHYL-
Theoretical properties:
molecular_formula: C12H17NO2
molecular_weight: 207.27 g/mol
exact_mass: 207.125928785 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 3
heavy_atom_count: 15
topological_polar_surface_area: 30.5 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: EDMA, also known as 3,4-ethylenedioxy-N-methylamphetamine or as MDMC, is a psychoactive drug of the phenethylamine, amphetamine, and EDxx families. It is an analogue of MDMA where the methylenedioxy ring has been replaced by an ethylenedioxy ring.
In his book PiHKAL (Phenethylamines I Have Known and Loved), the dose is listed as 150 to 250 mg orally and the duration as 3 to 5 hours. According to Shulgin, EDMA produces only mild effects that included paresthesia, nystagmus, a dozing state, hypnogogic imagery, and colored letters in the peripheral visual field. 
It has been found that EDMA acts as a non-neurotoxic serotonin releasing agent with moderately diminished potency relative to MDMA, and with negligible effects on dopamine release. However, subsequent research found that EMDA is a serotonin–norepinephrine–dopamine releasing agent (SNDRA) with EC50Tooltip half-maximal effective concentration values of 117 nM for serotonin release, 325 nM for norepinephrine release, and 597 nM for dopamine release in rat brain synaptosomes. Compared to MDMA, EDMA was about half as potent as a serotonin releaser, 4.5-fold less potent as a norepinephrine releaser, and 8-fold less potent as a dopamine releaser. The activities of the individual enantiomers of EDMA have also been assessed.
The chemical synthesis of EDMA has been described.
While commonly referred to as EDMA, Shulgin refers to this compound as both MDMC and EDMA in PiHKAL, calling the former a "Shulgin pet name" for the compound, and stating that the name "doesn't really make sense". MDMC commonly refers to a different analogue of MDMA, methylone.
SMILES: O=C(O)/C(=C/C(=O)O)/CC(=O)O
InChIKey: GTZCVFVGUGFEME-HNQUOIGGSA-N
Theoretical properties:
Physical properties:
Descriptions:
chebi: The <i>trans</i>-isomer of aconitic acid.
chembl: ACONITIC ACID is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
Compound: Oxalosuccinic acid
SMILES: O=C(O)C(=O)C(C(=O)O)CC(=O)O
InChIKey: UFSCUAXLTRFIDC-UHFFFAOYSA-N
Synonyms: Oxalosuccinic acid, 1948-82-9, 1-oxopropane-1,2,3-tricarboxylic acid, UNII-DFK99PW32K, Oxalbernsteinsaeure, DFK99PW32K, CHEBI:7815, 1,2,3-PROPANETRICARBOXYLIC ACID, 1-OXO-, RefChem:168807, (+-)-OXALOSUCCINIC ACID, OXALOSUCCINIC ACID, (+-)-, oxalosuccinate, bmse000251, SCHEMBL1052505, DTXSID30862799, (+/-)-OXALOSUCCINIC ACID, OXALOSUCCINIC ACID, (+/-)-, C05379, Q424172
Theoretical properties:
molecular_formula: C6H6O7
molecular_weight: 190.11 g/mol
exact_mass: 190.01135253 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 3
hydrogen_bond_acceptor_count: 7
rotatable_bond_count: 5
heavy_atom_count: 13
topological_polar_surface_area: 129 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Oxalosuccinic acid is a tricarboxylic acid consisting of 2-oxoglutaric acid having a further carboxy group at the 3-position. It is a substrate of the citric acid cycle. It has a role as a fundamental metabolite. It is functionally related to a 2-oxoglutaric acid. It is a conjugate acid of an oxalatosuccinate(3-).
chebi: A tricarboxylic acid consisting of 2-oxoglutaric acid having a further carboxy group at the 3-position. It is a substrate of the citric acid cycle.
wikipedia: Oxalosuccinic acid is a substrate of the citric acid cycle. It is acted upon by isocitrate dehydrogenase.  Salts and esters of oxalosuccinic acid are known as oxalosuccinates.
Oxalosuccinic acid/oxalosuccinate is an unstable 6-carbon intermediate in the tricarboxylic acid cycle. It's a keto acid, formed during the oxidative decarboxylation of isocitrate to alpha-ketoglutarate, which is catalyzed by the enzyme isocitrate dehydrogenase. Isocitrate is first oxidized by coenzyme NAD+ to form oxalosuccinic acid/oxalosuccinate. Oxalosuccinic acid is both an alpha-keto and a beta-keto acid (an unstable compound) and it is the beta-ketoic property that allows the loss of carbon dioxide in the enzymatic reaction in conversion to the five-carbon molecule 2-oxoglutarate.
Compound: Cyclopropylmescaline
SMILES: O(c1c(OC)cc(CCN)cc1OC)CC2CC2
InChIKey: LNTBHKZMYJTHTH-UHFFFAOYSA-N
Synonyms: Cyclopropylmescaline, 207740-23-6, D9268U4GS8, 4-(Cyclopropylmethoxy)-3,5-dimethoxybenzeneethanamine, 3,5-Dimethoxy-4-(cyclopropylmethoxy)phenethylamine, 2-(4-(cyclopropylmethoxy)-3,5-dimethoxyphenyl)ethanamine, CPM (PSYCHEDELIC), 2-[4-(cyclopropylmethoxy)-3,5-dimethoxyphenyl]ethanamine, RefChem:198593, 2-[4-(Cyclopropylmethoxy)-3,5-dimethoxyphenyl]ethan-1-amine, UNII-D9268U4GS8, Benzeneethanamine, 4-(cyclopropylmethoxy)-3,5-dimethoxy-, 2-(4-(Cyclopropylmethoxy)-3,5-dimethoxyphenyl)ethan-1-amine, CHEMBL421458, SCHEMBL20970869, DTXSID60658384, HIA74023, AKOS005930785, 3,5-dimethoxy-4-cyclopropylmethoxyphenethylamine, EN300-6743370, Q5198969
Theoretical properties:
molecular_formula: C14H21NO3
molecular_weight: 251.32 g/mol
exact_mass: 251.15214353 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 7
heavy_atom_count: 18
topological_polar_surface_area: 53.7 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: Cyclopropylmescaline (CPM), also known as 4-cyclopropylmethoxy-3,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and scaline families related to mescaline. It is taken orally and has a very long duration of 12 to 18 hours.