Analogs of alpha-Methylphenethylamine (Amphetamine). I. Synthesis and Pharmacological Activity of Some Methoxy and/or Methyl Analogs.
Ho, McIsaac, An, Tansey, Walker, Englert, Noel
Journal of Medicinal Chemistry 13, 1970, 26-30.
https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000453757-amphetamines_Noel.pdf" target="_blank" title="Download this file">

Abstract: A series of amphetamine derivatives substituted on the benzene ring with MeO and/or Me groups was synthesized. The pharmacological activity of these compounds was evaluated for toxicity, effects on barbiturate sleeping time, and ability to disrupt mouse behavior. Those which were active in behavioral disruption included 1-(2,5-dimethoxy-4-methylphenyl)-, 1-(2,4,5-trimethoxyphenyl)-, 1-(2,4-dimethoxy-3-methylphenyl)-, and 1-(3,4-methylenedioxyphenyl)-2-aminopropanes. In addition, 1-(3-methoxy-4-methylphenyl)-2-amino-propane, structurally resembling 1-(2,5)-dimethoxy-4-methylphenyl)-2-aminopropane (DOM), was found to be just as active and long lasting as DOM. The amphetamine derivatives either diminished or prolonged the barbiturate sleeping time. 1-(3,4-Methylenedioxyphenyl)-2-aminopropane and DOM were equally effective in decreasing the sleeping time, while 1-(2,4,6-trimethylphenyl)- and 1-(3,5-dimethyl-4-hydroxyphenyl)-2-amino-propanes were the most active in the potentiation of the sleeping time.

Besides the well known ones featuring also:
2-MeO-4-Me-amphetamine
3-MeO-4-Me-amphetamine  (MMA)
3,5-diMeO-amphetamine
2,3-diMeO-amphetamine
2,4-diMeO-3-Me-amphetamine
3,5-diMe-4-MeO-amphetamine
3,5-Me-4-OH-amphetamine
2,4,6-triMe-amphetamine

Does this mean that DOB was first synthesized by Nichols, and not by Shulgin?

Yes, but the first article about its human psychopharmacology was published by Shulgin, see Ref #8 from Nichols' article above, which corresponds to this one:

Post 495305

(Rhodium: "Shulgin: First Human Evaluation of DOB", Methods Discourse) Also see

Post 495313

(Rhodium: "Shulgin: Human Pharmacodynamics of DOB", Novel Discourse)

I find it very interesting indeed that 3-methoxy-4-methylamphetamine was found to be "just as active and long-lasting as DOM."

Does anyone else agree?

MMA is definitely less potent than DOM. SWIM found that MMA hydrochloride (orally) at 4 mg level produces only threshold effects, mostly physical (tension of facial muscles). Higher dosages are still untested.

4-Bromo-2,5-Dimethoxyphenylisopropylamine, a New Centrally Active Amphetamine Analog
A. T. Shulgin, T. Sargent and C. Naranjo

Pharmacology 5, 103–107 (1971)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/shulgin/shulgin.dob.pdf)

Abstract
A new centrally active halo-amine, 4-bromo-2,5-dimethoxyphenylisopropylamine, is described. In clinical evaluation it proved to enhance effectively both emotional and intellectual perception, without the imagery and perceptual distortions commonly encountered with many of the chemically related psychotomimetics. These properties suggest a potential valuable role in conjunction with psychotherapy.

This article has been referenced in the following post:

Post 432948

(Chimimanie: "DOI", Novel Discourse)

Azole, you've trien' to tell, MMA is an PSY- ... for your SWYL opinion and testin' it's not empathohene???

If you've an time for such lesses, pliz write PM to me (in russian pliz - cause this theme is my huge paine in da butt )...

PS for (everybee else around - sorry for my terrible english)...

 In clinical evaluation it proved to enhance effectively both emotional and intellectual perception, without the imagery and perceptual distortions commonly encountered with many of the chemically related psychotomimetics.



Errr? DOB not being visually active? Is that correct, or is there some wierd dosage-response curve?

You need to up the dosage of DOB to 2-3 times the minimum psychoactive dosage for any significant visuals to occur... And you can take over 10 times the minimum psychoactive dosage and the visual field is still not as clogged as it becomes on ~30mg 2C-B.

4-Bromo-2,5-Dimethoxyamphetamine: Psychoactivity, Toxic Effects and Analytical Methods
D. Delliou

Forensic Science International 21, 299-267 (1983)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/forensic/dob.forensic.review.pdf)

Summary
4-bromo-2,5-dimethoxyamphetamine (bromo-DMA) is a drug of special interest as it is available in forms which are seldom seen elsewhere in the world. Data of interest to the Forensic Chemist is summarized. The psychoactivity of bromo-DMA is discussed and a number of case histories involving higher doses are related. A description of dosage forms has been included and variations in drug concentration is discussed. Chemical properties and various methods of quantitative and qualitative analysis, eluding the use of high performance liquid chromatography, mass spectrometry and infrared spectroscopy are listed.