DOx

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Template:Short description

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File:2,5-DMA.svg
2,5-Dimethoxyamphetamine (2,5-DMA), the base chemical structure of the DOx family.

4-Substituted-2,5-dimethoxyamphetamines (DOx) is a chemical class of substituted amphetamine derivatives featuring methoxy groups at the 2- and 5- positions of the phenyl ring, and a substituent such as alkyl or halogen at the 4- position of the phenyl ring.[1][2] They are 4-substituted derivatives of 2,5-dimethoxyamphetamine (2,5-DMA, DOH) and are structurally related to the naturally occurring phenethylamine psychedelic mescaline.

The most well-known DOx drugs are DOM, DOI, DOB, DOET, and DOC.[3] DOI is widely used in scientific research.[2][4] DOM has been used as a recreational drug, while DOET was an experimental pharmaceutical drug.[5]

Most compounds of this class are potent and long-lasting psychedelic drugs, and act as selective 5-HT2A, 5-HT2B, and 5-HT2C receptor agonists.[6][7] A few bulkier derivatives such as DOAM have similarly high affinity for 5-HT2 receptors but have reduced activational efficacy and do not produce psychedelic effects.[2][6]

DOI has been found to have extraordinarily potent anti-inflammatory effects.[8][9][10] These properties are not shared by all other related drugs and appear to be mediated by functionally selective serotonin 5-HT2A receptor activation.[9][11] The anti-inflammatory effects of DOI and related drugs may have medical applications.[8][9]

Use

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Doses and durations of DOx drugs
Compound Chemical name Dosage Duration
DOAM 4-Amyl-2,5-dimethoxyamphetamine ≥5–40 mg Unknown
DOB 4-Bromo-2,5-dimethoxyamphetamine 1–3 mg 18–30 hours
DOBU 4-Butyl-2,5-dimethoxyamphetamine ≥1–10 mg Very long
DOBz (DOBN) 4-Benzyl-2,5-dimethoxyamphetamine Unknown Unknown
DOC 4-Chloro-2,5-dimethoxyamphetamine 1.5–5 mg 12–24 hours
DOEF 4-(2-Fluoroethyl)-2,5-dimethoxyamphetamine 2–3.5 mg 12–16 hours
DOET 4-Ethyl-2,5-dimethoxyamphetamine 2–6 mg 5–20 hours
DOF 4-Fluoro-2,5-dimethoxyamphetamine >18 mg Unknown
DOH (2,5-DMA) 2,5-Dimethoxyamphetamine 80–160 mg 6–8 hours
DOHx 4-Hexyl-2,5-dimethoxyamphetamine Unknown Unknown
DOI 4-Iodo-2,5-dimethoxyamphetamine 1.5–3 mg 16–30 hours
DOIB 4-Isobutyl-2,5-dimethoxyamphetamine 10–15 mg Unknown
DOIP 4-Isopropyl-2,5-dimethoxyamphetamine 20–30 mg Unknown
DOM 4-Methyl-2,5-dimethoxyamphetamine 3–10 mg 14–20 hours
DON 4-Nitro-2,5-dimethoxyamphetamine 3–4.5 mg 8–15 hours
DOPP 4-(3-Phenylpropyl)-2,5-dimethoxyamphetamine Unknown Unknown
DOPR 4-Propyl-2,5-dimethoxyamphetamine 2.5–5 mg 20–30 hours
DOSB 4-sec-Butyl-2,5-dimethoxyamphetamine 25–30 mg Very long
DOTB 4-tert-Butyl-2,5-dimethoxyamphetamine >25 mg Unknown
DOTFE 4-(2,2,2-Trifluoroethyl)-2,5-dimethoxyamphetamine >3 mg Unknown
DOTFM 4-(Trifluoromethyl)-2,5-dimethoxyamphetamine 0.3–1 mg Unknown
DOYN 4-Ethynyl-2,5-dimethoxyamphetamine 2–6 mg 10–15 hours
MEM 4-Ethoxy-2,5-dimethoxyamphetamine 20–50 mg 10–14 hours
Aleph (DOT) 4-Methylthio-2,5-dimethoxyamphetamine 5–10 mg 6–8 hours
Aleph-2 4-Ethylthio-2,5-dimethoxyamphetamine 4–8 mg 8–16 hours
Aleph-4 4-Isopropylthio-2,5-dimethoxyamphetamine 7–12 mg 12–20 hours
Aleph-6 4-Phenylthio-2,5-dimethoxyamphetamine ≥40 mg Very long
Aleph-7 4-Propylthio-2,5-dimethoxyamphetamine 4–7 mg 15–30 hours
G-1 3,4-Dimethyl-2,5-dimethoxyamphetamine 20–32 mg 18–24 hours
G-3 3,4-(Trimethylene)-2,5-dimethoxyamphetamine 12–18 mg 8–12 hours
G-5 3,4-Norbornyl-2,5-dimethoxyamphetamine 14–20 mg 16–30 hours
TMA-2 (2,4,5-TMA) 4-Methoxy-2,5-dimethoxyamphetamine 20–40 mg 8–12 hours
Refs: [2][12][13][3][14][15][16][17][18][19][20][21][22][23]

Side effects

DOx drugs like DOM have been associated with certain side effects that have not occurred to the same extent with other psychedelics like LSD.[5] Examples of such side effects include physical symptoms like sweating, tremors, and large increases in heart rate.[5]

Interactions

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Pharmacology

Pharmacodynamics

Actions

DOx drugs at the human 5-HT2 receptors
Compound Affinity (Ki, nM)
5-HT2A 5-HT2B 5-HT2C
2,5-DMATooltip 2,5-Dimethoxyamphetamine 211–2,502 1,039 104–>5,070
DOMTooltip 2,5-Dimethoxy-4-methylamphetamine 88–507.4 11.7 404–3,980
DOETTooltip 2,5-Dimethoxy-4-ethylamphetamine 12–100 28.8 107.2–108
DOPRTooltip 2,5-Dimethoxy-4-n-propylamphetamine 0.9 54.4 1.1
DOBUTooltip 2,5-Dimethoxy-4-n-butylamphetamine 5.4 ND 60
DOTBTooltip 2,5-Dimethoxy-4-t-butylamphetamine 3.7 24.6 2.2
DOAMTooltip 2,5-Dimethoxy-4-amylamphetamine 3.5 ND 75
DOHxTooltip 2,5-Dimethoxy-4-n-hexylamphetamine 0.1 30.3 0.7
DOFTooltip 2,5-Dimethoxy-4-fluoroamphetamine 41.7–378 227 28.7–792
DOCTooltip 2,5-Dimethoxy-4-chloroamphetamine 1.4–12 31.8 2.0–143
DOBTooltip 2,5-Dimethoxy-4-bromoamphetamine 0.6–41 26.9 1.3–78
DOITooltip 2,5-Dimethoxy-4-iodoamphetamine 0.7–165.4 20.0–335.9 2.4–48
TMA-2Tooltip 2,4,5-Trimethoxyamphetamine 57.9–584.2 154.4–307 87.7–4,062
MEMTooltip 2,5-Dimethoxy-4-ethoxyamphetamine 73.0–3,948 64.5–763 124–>10,000
Aleph-2Tooltip 2,5-Dimethoxy-4-ethylthioamphetamine 60.4 1.6 50.3
DOAcTooltip 2,5-Dimethoxy-4-acetylamphetamine 80.5 313 91.3
DONTooltip 2,5-Dimethoxy-4-nitroamphetamine 5.5 166 22.4
DOCNTooltip 2,5-Dimethoxy-4-cyanoamphetamine 45.7 774 1,011
DOBZTooltip 2,5-Dimethoxy-4-benzylamphetamine 0.4 35.0 1.0
M-154 94.2 341 68.1
D-367 88.5 521 514
QDOB 2,155 >10,000 6,298
Notes: The smaller the value, the more avidly the drug binds to the site. Refs: [24][25][7][6][26][27]

The DOx drugs act as agonists of the serotonin 5-HT2 receptors, including of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors.[6][28][7][2][3][29] Their psychedelic effects are thought to be mediated specifically by activation of the serotonin 5-HT2A receptor.[28][2]

In contrast to other amphetamines, DOx drugs like DOC, DOET, and DOM are inactive as monoamine releasing agents and reuptake inhibitors.[30][31][6] Some of the DOx drugs, including DOB, DOET, DOI, and DOM, are agonists of the rat, rhesus monkey, and/or human trace amine-associated receptor 1 (TAAR1) with varying potencies.[32][33]

Effects

In contrast to amphetamines like (–)-cathinone, but similarly to mescaline, DOM has shown no stimulant-like or reinforcing effects in rhesus monkeys.[34][35][36][37] Conversely however, DOC has shown reinforcing effects, including conditioned place preference (CPP) and self-administration, in rodents similarly to methamphetamine.[38] This is analogous to other findings in which various 2C and NBOMe drugs have been found to produce brain dopaminergic elevations and reinforcing effects in rodents.[39][40][41][42][43][44][45]

Pharmacokinetics

The DOx drugs are orally active and many have doses in the range of 1 to 10Script error: No such module "String".mg and durations in the range of 8 to 30Script error: No such module "String".hours.[14][3][2][12][5] Some DOx drugs, such as DOM and DOB, appear to have durations that increase non-linearly with dosage, for instance 8Script error: No such module "String".hours at lower doses and as long as 30Script error: No such module "String".hours or even up to 3 or 4Script error: No such module "String".days at higher doses.[5][15] This suggests that the pathways mediating the metabolism of these drugs can saturate.[5] The DOx drugs are metabolized primarily by O-demethylation.[3] However, DOM is primarily metabolized by hydroxylation at its methyl group.[3]

History

DOM was the first psychedelic of the DOx series to be discovered.[4] It was first synthesized by Alexander Shulgin at Dow Chemical Company in 1963, who had had his first psychedelic experience, with mescaline (3,4,5-trimethoxyphenethylamine), in 1960.[4][5][16] Shulgin personally tried DOM on January 4, 1964 and discovered its psychedelic effects.[46][4][5][16] 2,4,5-Trimethoxyamphetamine (TMA-2; "DOMeO") had been synthesized by Bruckner in 1933, but its psychedelic effects were not described until Shulgin tried the compound and reported its effects in the scientific literature in 1964.[22][47][48] Prior to this, 3,4,5-trimethoxyamphetamine (TMA; α-methylmescaline) had been synthesized by Hey in 1947, being found by him to produce euphoria, and was described by Peretz and colleagues in 1955 as clearly producing psychedelic effects.[22][49][50][51]

Following his discovery of DOM, Shulgin developed DOET and found that at low doses it was a remarkable "psychic energizer" without producing psychedelic effects at these doses.[5] Dow Chemical Company decided to move forward with clinical trials of DOET as a potential pharmaceutical drug for such purposes.[5] Shulgin and Dow Chemical Company filed a patent for DOET in 1966, although it was not published until 1970.[5][4][52] Dow Chemical Company tasked Solomon H. Snyder at Johns Hopkins University with clinically studying DOET.[5]

In April 1967, following the banning of LSD in California in 1966, DOM emerged as a street drug and legal LSD alternative with the name "STP" (allegedly short for "Serenity, Tranquility, and Peace") in the Haight-Ashbury district in San Francisco.[5][53] This occurred due to DOM being publicly distributed for free in the form of high-dose tablets by LSD distributor Owsley Stanley, who had personally learned of DOM from Shulgin.[5][53] It is unclear why Shulgin provided information about DOM to Stanley, since doing so had the potential to risk Shulgin's professional career and the DOET clinical studies.[5][53] One possibility is that Dow Chemical Company was not further looking into DOM and Shulgin thought that it was a promising drug that would otherwise be forgotten.[5] In any case, street use of DOM was short-lived because the tablets caused a public health crisis due to them often producing very long durations (up to 3–4Script error: No such module "String".days), intense experiences, worrying physical side effects, and hospitalizations.[5] DOM was first reported on in the media and scientific literature in 1967 as a result of the crisis.[5][54][55] DOM became illegal in the United States in 1968.[5]

Dow Chemical Company terminated its clinical research program on DOET due to the DOM public health crisis.[5] DOET was subsequently first described in the literature by Snyder and colleagues in 1968.[55] Snyder continued to be interested in DOET as a potential medicine, but it was never further developed.[55] Snyder also described 2,5-dimethoxyamphetamine (2,5-DMA), which had been synthesized and tested by Shulgin, in the literature in 1968.[56] DOM and DOET were further described in the scientific literature by Shulgin in 1969.[57][4][5] In addition, Shulgin discussed DOM, DOET, TMA-2, and 2,5-DMA in a book chapter on hallucinogens published in 1970.[58]

The earlier DOx drugs like DOM and DOET were subsequently followed by DOB, which was developed by Shulgin and colleagues like Claudio Naranjo, in 1971,[4][59] and by DOI, DOC, and a few other analogues, which were developed by another research group, in 1973.[4][60] After this, numerous other DOx drugs were synthesized and characterized, both by Shulgin and other scientists.[22][13][15][12][16][61][2]

Following its discovery, DOI has become widely used in scientific research in the study of the serotonin 5-HT2 receptors.[4][2]

List of DOx drugs

The DOx family includes the following members:

Template:Sticky

Structure Name Abbreviation CAS # Ref
File:2,5-DMA.svg 2,5-Dimethoxyamphetamine 2,5-DMA 2801-68-5
File:DOAM.svg 2,5-Dimethoxy-4-amylamphetamine DOAM 63779-90-8
File:DOB-racemic-skeletal.svg 2,5-Dimethoxy-4-bromoamphetamine DOB 64638-07-9
File:DOBU.svg 2,5-Dimethoxy-4-butylamphetamine DOBU 63779-89-5
File:DOC-racemic-skeletal.svg 2,5-Dimethoxy-4-chloroamphetamine DOC 123431-31-2
File:MEM.svg 2,5-Dimethoxy-4-ethoxyamphetamine MEM 16128-88-4
File:DOMOM structure.png 2,5-Dimethoxy-4-(methoxymethyl)amphetamine DOMOM 260810-10-4 [62]
File:DOMOE structure.png 2,5-Dimethoxy-4-(ethoxymethyl)amphetamine DOMOE 930836-81-0
File:2,5-Dimethoxy-4-ethylamphetamine.svg 2,5-Dimethoxy-4-ethylamphetamine DOET 22004-32-6
File:2,5-dimethoxy-4-ethylthioamphetamine.svg 2,5-Dimethoxy-4-ethylthioamphetamine Aleph-2 185562-00-9
File:2,5-Dimethoxy-4-fluoroamphetamine.svg 2,5-Dimethoxy-4-fluoroamphetamine DOF 125903-69-7
File:2,5-Dimethoxy-4-(2-fluoroethyl)amphetamine.svg 2,5-Dimethoxy-4-(2-fluoroethyl)amphetamine DOEF 121649-01-2
File:DOPF structure.png 2,5-Dimethoxy-4-(3-fluoropropyl)amphetamine DOPF ?
File:DOI-racemic-skeletal.svg 2,5-Dimethoxy-4-iodoamphetamine DOI 42203-78-1
File:Aleph-4.svg 2,5-Dimethoxy-4-isopropylthioamphetamine Aleph-4 123643-26-5
File:Trimethoxyamphetamine-2.svg 2,4,5-Trimethoxyamphetamine TMA-2 (DOMeO) 1083-09-6
File:2,5-Dimethoxy-4-methylamphetamine.svg 2,5-Dimethoxy-4-methylamphetamine DOM 15588-95-1
File:2,5-dimethoxy-4-methylthioamphetamine.svg 2,5-Dimethoxy-4-methylthioamphetamine Aleph-1 (DOT) 61638-07-1
File:2,5-Dimethoxy-4-nitroamphetamine.svg 2,5-Dimethoxy-4-nitroamphetamine DON 67460-68-8
File:Aleph-6.svg 2,5-Dimethoxy-4-phenylthioamphetamine Aleph-6 952006-44-9
File:DOBZ structure.png 2,5-Dimethoxy-4-benzylamphetamine DOBz 125903-73-3
File:DO3MeOBZ structure.png 2,5-Dimethoxy-4-(3-methoxybenzyl)amphetamine DO3MeOBZ 930836-90-1 [63]
File:DOTHFM structure.png 2,5-Dimethoxy-4-[(tetrahydrofuran-2-yl)methyl]amphetamine DOTHFM 930776-12-8
File:2,5-Dimethoxy-4-propylamphetamine.svg 2,5-Dimethoxy-4-propylamphetamine DOPR 63779-88-4
File:DOiPR structure.png 2,5-Dimethoxy-4-isopropylamphetamine DOiP 42306-96-7
File:2,5-dimethoxy-4-propylthioamphetamine.svg 2,5-Dimethoxy-4-propylthioamphetamine Aleph-7 207740-16-7
File:DODFM structure.png 2,5-Dimethoxy-4-(difluoromethyl)amphetamine DODFM ?
File:2,5-Dimethoxy-4-trifluoromethylamphetamine.svg 2,5-Dimethoxy-4-trifluoromethylamphetamine DOTFM 159277-07-3
File:DOTFE structure.png 2,5-Dimethoxy-4-(2,2,2-trifluoroethyl)amphetamine DOTFE ? [64]
File:DOCN structure.png 2,5-Dimethoxy-4-cyanoamphetamine DOCN 125903-74-4 [65]
File:DOYN structure.png 2,5-Dimethoxy-4-ethynylamphetamine DOYN 633290-70-7 [66]
File:DOAC structure.png 2,5-Dimethoxy-4-acetylamphetamine DOAc ?
File:DOIB structure.png 2,5-Dimethoxy-4-isobutylamphetamine DOIB 89556-64-9
File:DOSB structure.png 2,5-Dimethoxy-4-sec-butylamphetamine DOSB 89556-71-8
File:DOTB structure.png 2,5-Dimethoxy-4-tert-butylamphetamine DOTB 41538-42-5
File:DOHX structure.png 2,5-Dimethoxy-4-hexylamphetamine DOHx ?
File:DOCT structure.png 2,5-Dimethoxy-4-octylamphetamine DOCT ?
File:4-PhPr-2,5-DMA.svg 4-(3-Phenylpropyl)-2,5-dimethoxyamphetamine DOPP ?
File:4-Methallyloxy-2,5-dimethoxyamphetamine.svg 4-Methallyloxy-2,5-dimethoxyamphetamine MMALM ? [67]
File:4-Allyloxy-2,5-dimethoxyamphetamine.svg 4-Allyloxy-2,5-dimethoxyamphetamine MALM ? [67]
File:4-(2-Fluoroethoxy)-2,5-dimethoxyamphetamine.svg 4-(2-Fluoroethoxy)-2,5-dimethoxyamphetamine MFEM ? [67]
File:4-(2,2-Difluoroethoxy)-2,5-dimethoxyamphetamine.svg 4-(2,2-Difluoroethoxy)-2,5-dimethoxyamphetamine MDFEM ? [67]
File:4-(2,2,2-Trifluoroethoxy)-2,5-dimethoxyamphetamine.svg 4-(2,2,2-Trifluoroethoxy)-2,5-dimethoxyamphetamine MTFEM ? [67]
File:4-Isopropoxy-2,5-dimethoxyamphetamine.svg 4-Isopropoxy-2,5-dimethoxyamphetamine MIPM ? [67]

Related compounds

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A number of additional compounds are known with alternative substitutions:

Template:Sticky

Structure Name Abbreviation CAS #
File:Beatrice (psychedelic).png Dimethoxymethamphetamine ("Beatrice") N-Methyl-DOM 92206-37-6
File:Methyl-DOB.png 2,5-Dimethoxy-4-iodo-N-methylamphetamine N-Methyl-DOB 155638-80-5
File:N-Methyl-DOI.svg 2,5-Dimethoxy-4-iodo-N-methylamphetamine N-Methyl-DOI ?
File:IDNNA.png 2,5-Dimethoxy-4-iodo-N,N-dimethylamphetamine IDNNA 67707-78-2
File:DMMDA.svg 2,5-Dimethoxy-3,4-methylenedioxyamphetamine DMMDA 15183-13-8
File:Ganesha.svg 2,5-Dimethoxy-3,4-dimethylamphetamine ("Ganesha") 3-Methyl-DOM 207740-37-2
File:3C-G-3.png 2,5-Dimethoxy-3,4-trimethylenylamphetamine G-3 ?
File:3C-G-4.png 2,5-Dimethoxy-3,4-tetramethylenylamphetamine G-4 ?
File:DOG5 structure.png 2,5-Dimethoxy-3,4-norbornylamphetamine G-5 ?
File:3C-G-N.png 1,4-Dimethoxynaphthyl-2-isopropylamine G-N ?
File:DOGO structure.png 1-(5,8-Dimethoxy-3,4-dihydro-1H-isochromen-7-yl)propan-2-amine[68] G-O 774538-38-4
File:DODC structure.png 2,5-Dimethoxy-3,4-dichloroamphetamine DODC 1373918-65-0
File:2,6-dimethoxy-4-methylamphetamine.svg 2,6-Dimethoxy-4-methylamphetamine ψ-DOM 80888-36-4
File:2,3,4,5-Tetramethoxyamphetamine.svg 2,3,4,5-Tetramethoxyamphetamine TeMA 23693-26-7
File:DOB-FLY structure.png 1-(4-Bromo-2,3,6,7-tetrahydrofuro[2,3-f][1]benzofuran-8-yl)propan-2-amine DOB-FLY 219986-75-1
File:R-Bromo-DragonFLY.svg Bromo-DragonFLY DOB-DFLY 502759-67-3
File:DMCPA.svg 2,5-Dimethoxy-4-methylphenylcyclopropylamine DMCPA 15183-13-8
File:WO2021-0137908-1 structure.png 3-(4-Bromo-2,5-dimethoxyphenyl)azetidine ZC-B[69] 2641630-65-9
File:DOM-CR.svg 5,8-Dimethoxy-7-methyl-1,2,3,4-tetrahydroisoquinoline DOM-CR (DOM-THIQ) 228997-46-4
File:DOB-CR.svg 5,8-Dimethoxy-7-bromo-1,2,3,4-tetrahydroisoquinoline DOB-CR (DOB-THIQ) ?
File:N-Methyl-DOM-CR.svg 2,7-Dimethyl-5,8-dimethoxy-1,2,3,4-tetrahydroisoquinoline N-Methyl-DOM-CR (Beatrice-CR) ?
File:DOM-AI.svg 4,7-Dimethoxy-5-methyl-2-aminoindane DOM-AI 52904-71-9
File:DOM-AT.svg 5,8-Dimethoxy-6-methyl-2-aminotetralin DOM-AT 53609-01-1
File:CT-5126 v2.svg 6,8-Dichloro-5-methoxy-3,4-dihydro-2H-1-benzopyran-3-amine CT-5126 ?
File:TFMBOX.svg 7-Methoxy-8-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzoxepin-4-amine TFMBOX 774160-02-0
File:DOM-NBOMe.svg N-(2-Methoxybenzyl)-2,5-dimethoxy-4-methylamphetamine[70] DOM-NBOMe 2836395-73-2
File:DOB-NBOMe structure.png N-(2-Methoxybenzyl)-2,5-dimethoxy-4-bromoamphetamine[71] DOB-NBOMe ?
File:DOI-NBOMe structure.png N-(2-Methoxybenzyl)-2,5-dimethoxy-4-iodoamphetamine[72] DOI-NBOMe ?
File:SS9b structure.png 2-(2,5-Dimethoxy-4-bromobenzyl)-6-(2-methoxyphenyl)piperidine DMBMPP (juncosamine) 1391499-52-7
File:DOM-NDEPA structure.png N-Diethylaminocarbonylethyl-2,5-dimethoxy-4-methylamphetamine DOM-NDEPA ?
File:DOB-NDEPA structure.png N-Diethylaminocarbonylethyl-2,5-dimethoxy-4-bromoamphetamine DOB-NDEPA ?
File:DOI-NDEPA structure.png N-Diethylaminocarbonylethyl-2,5-dimethoxy-4-iodoamphetamine DOI-NDEPA ?
File:DOTFM-NDEPA structure.png N-Diethylaminocarbonylethyl-2,5-dimethoxy-4-(trifluoromethyl)amphetamine DOTFM-NDEPA ?
File:TMA-2-NDEPA structure.png N-Diethylaminocarbonylethyl-2,4,5-trimethoxyamphetamine TMA-2-NDEPA ?
File:ZDCM-04 structure.png 1,3-Dimethyl-7-{2-[1-(2,5-dimethoxy-4-chlorophenyl)propan-2-ylamino]ethyl}purine-2,6-dione ZDCM-04 ?

See also

References

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  69. ↑ Kristensen J, et al. 5-HT2A Agonists for Use in Treatment of Depression. Patent US 2021/0137908
  70. ↑ Script error: No such module "citation/CS1".
  71. ↑ Script error: No such module "citation/CS1".
  72. ↑ Script error: No such module "citation/CS1".

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External links

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