Biomaterial Database

Synthesis and evaluation of 2,3-dihydrobenzofuran analogues of the hallucinogen 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane: drug discrimination studies in rats. 1986

D E Nichols, and A J Hoffman, and R A Oberlender, and R M Riggs

Two analogues, 6-(2-aminopropyl)-5-methoxy-2,3-dihydrobenzofuran and 6-(2-aminopropyl)-5-methoxy-2-methyl-2,3-dihydrobenzofuran, of the hallucinogenic agent 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM) were synthesized and tested in the two-lever drug discrimination paradigm. In rats trained to discriminate saline from LSD tartrate (0.08 mg/kg), stimulus generalization occurred to both of the 2,3-dihydrobenzofuran analogues but at doses more than 10-fold higher than for DOM. A possible explanation for this dramatic attenuation of LSD-like activity could involve a highly directional electrophilic binding site on the receptor that cannot accept the orientation of the unshared electron pairs on the heterocyclic oxygen atom in the benzofurans.

UI	MeSH Term	Description	Entries
D008238	Lysergic Acid Diethylamide	Semisynthetic derivative of ergot (Claviceps purpurea). It has complex effects on serotonergic systems including antagonism at some peripheral serotonin receptors, both agonist and antagonist actions at central nervous system serotonin receptors, and possibly effects on serotonin turnover. It is a potent hallucinogen, but the mechanisms of that effect are not well understood.	LSD,Lysergide,LSD-25,Lysergic Acid Diethylamide Tartrate,Acid Diethylamide, Lysergic,Diethylamide, Lysergic Acid,LSD 25
D008297	Male		Males
D008968	Molecular Conformation	The characteristic three-dimensional shape of a molecule.	Molecular Configuration,3D Molecular Structure,Configuration, Molecular,Molecular Structure, Three Dimensional,Three Dimensional Molecular Structure,3D Molecular Structures,Configurations, Molecular,Conformation, Molecular,Conformations, Molecular,Molecular Configurations,Molecular Conformations,Molecular Structure, 3D,Molecular Structures, 3D,Structure, 3D Molecular,Structures, 3D Molecular
D011919	Rats, Inbred Strains	Genetically identical individuals developed from brother and sister matings which have been carried out for twenty or more generations or by parent x offspring matings carried out with certain restrictions. This also includes animals with a long history of closed colony breeding.	August Rats,Inbred Rat Strains,Inbred Strain of Rat,Inbred Strain of Rats,Inbred Strains of Rats,Rat, Inbred Strain,August Rat,Inbred Rat Strain,Inbred Strain Rat,Inbred Strain Rats,Inbred Strains Rat,Inbred Strains Rats,Rat Inbred Strain,Rat Inbred Strains,Rat Strain, Inbred,Rat Strains, Inbred,Rat, August,Rat, Inbred Strains,Rats Inbred Strain,Rats Inbred Strains,Rats, August,Rats, Inbred Strain,Strain Rat, Inbred,Strain Rats, Inbred,Strain, Inbred Rat,Strains, Inbred Rat
D004193	Discrimination Learning	Learning that is manifested in the ability to respond differentially to various stimuli.	Discriminative Learning,Discrimination Learnings,Discriminative Learnings,Learning, Discrimination,Learning, Discriminative
D004290	DOM 2,5-Dimethoxy-4-Methylamphetamine	A psychedelic phenyl isopropylamine derivative, commonly called DOM, whose mood-altering effects and mechanism of action may be similar to those of LSD.	2,5-Dimethoxy-4-Methylamphetamine,2,5-Dimethoxy-4-Methylamphetamine (DOM),1-(2,5-Dimethoxy-4-Methylphenyl)-2-Aminopropane,2 5 DOM,2,5-Dimethoxy-4-Methylamphetamine Hydrochloride, (+,-)-Isomer,2,5-Dimethoxy-4-Methylamphetamine Hydrochloride, (R)-Isomer,2,5-Dimethoxy-4-Methylamphetamine Hydrochloride, (S)-Isomer,2,5-Dimethoxy-4-Methylamphetamine, (+,-)-Isomer,2,5-Dimethoxy-4-Methylamphetamine, (R)-Isomer,2,5-Dimethoxy-4-Methylamphetamine, (S)-Isomer,2,5-Dimethoxy-4-Methylamphetamine, Hydrochloride,2,5 Dimethoxy 4 Methylamphetamine,2,5-Dimethoxy-4-Methylamphetamine, DOM,DOM 2,5 Dimethoxy 4 Methylamphetamine
D006213	Hallucinogens	Drugs capable of inducing illusions, hallucinations, delusions, paranoid ideations, and other alterations of mood and thinking. Despite the name, the feature that distinguishes these agents from other classes of drugs is their capacity to induce states of altered perception, thought, and feeling that are not experienced otherwise.	Hallucinogen,Hallucinogenic Agent,Hallucinogenic Drug,Hallucinogenic Substance,Psychedelic,Psychedelic Agent,Psychedelic Agents,Psychotomimetic Agent,Psychotomimetic Agents,Hallucinogenic Agents,Hallucinogenic Drugs,Hallucinogenic Substances,Psychedelics,Agent, Hallucinogenic,Agent, Psychedelic,Agent, Psychotomimetic,Agents, Hallucinogenic,Agents, Psychedelic,Agents, Psychotomimetic,Drug, Hallucinogenic,Drugs, Hallucinogenic,Substance, Hallucinogenic,Substances, Hallucinogenic
D000662	Amphetamines	Analogs or derivatives of AMPHETAMINE. Many are sympathomimetics and central nervous system stimulators causing excitation, vasopressin, bronchodilation, and to varying degrees, anorexia, analepsis, nasal decongestion, and some smooth muscle relaxation.
D000818	Animals	Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA.	Animal,Metazoa,Animalia
D001572	Benzofurans	Compounds that contain a BENZENE ring fused to a furan ring.	Coumarones,Diphenylbenzofuran