Civil Rights
Movements, leaders, victories and the continuing fight for equality.
Explore the people, places, events, achievements, struggles and stories that shaped our journey.
Movements, leaders, victories and the continuing fight for equality.
Innovation, patents, science, technology and world-changing contributions.
Pioneers, champions, Negro Leagues, records, activism and excellence.
Meet the people whose lives, choices and achievements shaped the journey.
Black towns, communities, institutions and places where history happened.
Moments that changed communities, movements, institutions and the nation.
Katherine Johnson’s mathematical calculations helped guide some of America’s most important early space missions while she confronted the racial and gender barriers faced by Black women in twentieth-century America.
MORE →Reflects the personal views, recollections, and perspective of the author, Mike Davis.
This is a personal recollection on the Move fire on May 13, 1985
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| Other names | N-HO-DOM; 4-Methyl-2,5-dimethoxy-N-hydroxyamphetamine; 2,5-Dimethoxy-4-methyl-N-hydroxyamphetamine; DOM-OH |
| Drug class | Possible serotonergic psychedelic or hallucinogen |
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| Formula | C12H19NO3 |
| Molar mass | 225.288 g·mol−1 |
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N-Hydroxy-DOM, also known as 4-methyl-2,5-dimethoxy-N-hydroxyamphetamine or as DOM-OH, is a possible psychedelic drug of the phenethylamine, amphetamine, and DOx families related to DOM.[1][2][3] It is the N-hydroxy derivative of DOM.[1][2][3] The drug was not included nor mentioned by Alexander Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved) and its properties and effects in humans are unknown.[4][3] N-Hydroxy-DOM was reported to produce DOM-like behavioral and physiological effects in rats, including pupil dilation and hypolocomotion among others, but was 6-fold less potent than DOM in this species.[1][5] It also appears to be a metabolite of DOM formed by the liver in rabbits.[2] Other N-hydroxy derivatives of phenethylamines such as the HOT-x series like HOT-2 (N-hydroxyl-2C-T-2) as well as MDOH (N-hydroxy-MDA) may act as prodrugs of their N-unsubstituted analogues.[4] The chemical synthesis of N-hydroxy-DOM has been described.[5] N-Hydroxy-DOM was first described in the scientific literature by Ronald Coutts and Jerry Malicky by 1973.[5][6] It is a controlled substance in Canada under phenethylamine blanket-ban language.[7]
One other active substitution on nitrogen is the N-hydroxy group. N-Hydroxylation of III gives a compound possessing clinical activity (66). Coutts and Malicky (72) evaluated several congeners of II. One, the N-hydroxy derivative (XXI), elicited behavioral effects in rats but at about six times the dosage required for II.
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N-Hydroxy-DOM, also known as 4-methyl-2,5-dimethoxy-N-hydroxyamphetamine or as DOM-OH, is a possible psychedelic drug of the phenethylamine, amphetamine, and DOx families related to DOM. It is the N-hydroxy derivative of DOM. The drug was not included nor mentioned by Alexander Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved) and its properties and effects in humans are unknown. N-Hydroxy-DOM was reported to produce DOM-like behavioral and physiological effects in rats, including pupil dilation and hypolocomotion among others, but was 6-fold less potent than DOM in this species. It also appears to be a metabolite of DOM formed by the liver in rabbits. Other N-hydroxy derivatives of phenethylamines such as the HOT-x series like HOT-2 (N-hydroxyl-2C-T-2) as well as MDOH (N-hydroxy-MDA) may act as prodrugs of their N-unsubstituted analogues. The chemical synthesis of N-hydroxy-DOM has been described. N-Hydroxy-DOM was first described in the scientific literature by Ronald Coutts and Jerry Malicky by 1973. It is a controlled substance in Canada under phenethylamine blanket-ban language.
3,4-Methylenedioxy-N-hydroxy-N-methylamphetamine, also known as MDMOH, MDHMA, or FLEA, is an entactogen, psychedelic, and stimulant of the phenethylamine, amphetamine, and MDxx families. It is the N-hydroxy homologue of MDMA ("Ecstasy"), and the N-methyl homologue of MDOH.
N-Hydroxy-AMT, or N-HO-AMT, also known as N-hydroxy-α-methyltryptamine, is a possible psychedelic drug of the tryptamine and α-alkyltryptamine families related to α-methyltryptamine (AMT). It is the N-hydroxy derivative of AMT. The drug was not mentioned in Alexander Shulgin's 1997 book TiHKAL (Tryptamines I Have Known and Loved) and its properties and effects in humans are unknown. In preclinical research, N-hydroxy-AMT produces stimulant-like effects in mice such as hyperlocomotion and antagonism of hexobarbital-induced sleeping time, pressor effects in cats, and a psychedelic-like rage reaction in cats. Unlike AMT, it is not a monoamine oxidase inhibitor (MAOI) in vitro. N-Hydroxy derivatives of phenethylamines such as the HOT-x series like HOT-2 as well as MDOH may act as prodrugs of their N-unsubstituted forms. The chemical synthesis and analytical detection of N-hydroxy-AMT have been described. N-Hydroxy-AMT was first described in the scientific literature by F. Benington and colleagues in 1965. It is not a controlled substance in Canada as of 2025.
3,4-Methylenedioxy-N-hydroxyamphetamine (MDOH, MDH), also known as N-hydroxy-MDA, is an entactogen, psychedelic, and stimulant of the phenethylamine, amphetamine, and MDxx families. It is the N-hydroxy homologue of MDA, and the N-desmethyl homologue of FLEA (MDMOH).
Before the 1921 destruction of Tulsa’s Greenwood District, Black residents had created a remarkable center of business and community life. The district included stores, professional offices, entertainment venues and homes owned by Black citizens. Understanding Greenwood means learning what was built—not only what was burned.
MORE →Brown v. Board of Education in 1954.