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Beatrice (drug)

Psychoactive drug


Psychoactive drug

FieldValue
Watchedfieldschanged
verifiedrevid413881888
drug_nameBeatrice
imageBeatrice.svg
image_classskin-invert-image
width200px
image2Beatrice-3d-sticks.png
image_class2bg-transparent
width2225px
routes_of_administrationOral
classSerotonin receptor modulator; Psychoactive drug; Stimulant
ATC_prefixNone
duration_of_action6–10 hours
CAS_number_Ref
CAS_number92206-37-6
PubChem212480
ChemSpiderID_Ref
ChemSpiderID184247
UNII_Ref
UNII4TM7A9W7KW
ChEMBL_Ref
ChEMBL19044
synonymsBEATRICE; Béa; 4-Methyl-2,5-dimethoxy-N-methylamphetamine; 2,5-Dimethoxy-4-methyl-N-methylamphetamine; 2,5-Dimethoxy-4,N-dimethylamphetamine; N-Methyl-DOM; MDO-D; MDOM
IUPAC_name1-(2,5-dimethoxy-4-methylphenyl)-N-methylpropan-2-amine
C13H=21N=1O=2
SMILESO(c1cc(c(OC)cc1CC(NC)C)C)C
StdInChI_Ref
StdInChI1S/C13H21NO2/c1-9-6-13(16-5)11(7-10(2)14-3)8-12(9)15-4/h6,8,10,14H,7H2,1-5H3
StdInChIKey_Ref
StdInChIKeyIWYGVDBZCSCJGT-UHFFFAOYSA-N

| Drugs.com =

| elimination_half-life =

Beatrice, also known as 4-methyl-2,5-dimethoxy-N-methylamphetamine or as N-methyl-DOM, MDOM, or MDO-D, is a psychoactive drug of the phenethylamine, amphetamine, and DOx families. It is a substituted methamphetamine and a homologue of 2,5-dimethoxy-4-methylamphetamine (DOM).

Use and effects

In Alexander Shulgin's book PiHKAL (Phenethylamines I Have Known and Loved), the minimum dose is listed as 30mg, and the duration is listed as 6 to 10hours. Beatrice produces a vague feeling of openness and receptiveness, and causes a stimulative effect. It also causes diarrhea. The drug is one of Shulgin's "ten classic ladies", a series of methylated DOM derivatives.

Interactions

Pharmacology

Pharmacodynamics

Beatrice shows affinity for serotonin receptors. Its affinities (Ki) were 415nM for the 5-HT2 receptor and 3,870nM for the 5-HT1 receptor. The affinity of Beatrice for the serotonin 5-HT2 receptor was about 4-fold lower than that of DOM. Functional activities were not reported.

Beatrice substituted for DOM in rodent drug discrimination tests, albeit with relatively low potency.

Chemistry

Synthesis

The chemical synthesis of Beatrice has been described.

Analogues

Analogues of Beatrice include N-methyl-DOET, N-methyl-DOI (N-Me-DOI), N-methyl-DOB, and IDNNA (N,N-dimethyl-DOI). N-Methyl-DOI is a potent agonist of the serotonin 5-HT2A receptor similarly to DOI, but with several-fold reduced potency and slightly reduced efficacy.

History

Beatrice was first described in the scientific literature by Beng T. Ho and colleagues in 1970. Subsequently, it was described in greater detail by Alexander Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).

Society and culture

Canada

Beatrice is a controlled substance in Canada under phenethylamine blanket-ban language.

United States

In the United States, Beatrice is a Schedule I isomer of DOET.

References

References

  1. [http://www.erowid.org/library/books_online/pihkal/pihkal011.shtml Beatrice Entry in ''PiHKAL'']
  2. (2011). "The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds". Transform Press.
  3. "Triple Goddess of the Night". British Neuroscience Association Bulletin.
  4. (January 1987). "Central serotonin receptors as targets for drug research". Journal of Medicinal Chemistry.
  5. (June 1984). "5-HT1 and 5-HT2 binding properties of derivatives of the hallucinogen 1-(2,5-dimethoxyphenyl)-2-aminopropane (2,5-DMA)". European Journal of Pharmacology.
  6. (1989). "Stimulus properties of hallucinogenic phenalkylamines and related designer drugs: formulation of structure-activity relationships". NIDA Research Monograph.
  7. (2013). "Phenethylamine: von der Struktur zur Funktion". Nachtschatten-Verlag.
  8. (16 January 2013). "Mapping the binding site of the 5-HT2A receptor using mutagenesis and ligand libraries: Insights into the molecular actions of psychedelics". Purdue University.
  9. (January 1970). "Amphetamine analogs. II. Methylated phenethylamines". Journal of Medicinal Chemistry.
  10. "Controlled Drugs and Substances Act".
  11. (January 2026). "Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026)". U.S. [[Department of Justice]]: [[Drug Enforcement Administration]] (DEA): Diversion Control Division.
  12. [[Drug Enforcement Administration]]. (3 December 2007). "Definition of “Positional Isomer” as It Pertains to the Control of Schedule I Controlled Substances".
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