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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.^[2] It is the N–hydroxy homologue of MDA, and the N–desmethyl homologue of FLEA (MDMOH).^[1]

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin listed the dose range as 100 to 160 mg orally and its duration as approximately 3 to 6 hours.^[1] He describes MDOH as being very psychedelic and producing increased pleasure in beauty and nature.^[1] Shulgin also mentioned several negative side effects also seen with MDMA (“Ecstasy”) such as difficulty urinating and internal dryness.^[1] He has noted that the properties and effects of MDOH are very similar or near-identical to those of MDA and that MDOH might be converted into MDA in the body.^[1]

Interactions

Chemistry

Synthesis

The chemical synthesis of MDOH has been described.^[1]

Analogues

Analogues of MDOH include MDA and FLEA (MDMOH), among others.^[1]

Society and culture

3,4-Methylenedioxy-N-hydroxyaMphetaMine

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Use and effects

Interactions

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Synthesis

The chemical synthesis of MDOH has been described.^[1]

Analogues

Analogues of MDOH include MDA and FLEA (MDMOH), among others.^[1]

Society and culture

Legal status

Canada

MDOH is a controlled substance in Canada.^[3]

United States

MDOH is a schedule I controlled substance in the United States.^[4]

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Use and effects

Interactions

Chemistry

Synthesis

The chemical synthesis of MDOH has been described.^[1]

Analogues

Analogues of MDOH include MDA and FLEA (MDMOH), among others.^[1]

Society and culture

Legal status

Canada

MDOH is a controlled substance in Canada.^[3]

United States

MDOH is a schedule I controlled substance in the United States.^[4]

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Product Description

N-Hydroxy-3,4-methylenedioxyamphetamine is a novel and potent bioactive compound

Biological Activity I Assay Protocols (From Reference)

Additional Infomation	N-Hydroxy-3,4-methylenedioxyamphetamine is a Category 1 controlled substance under the U.S. Drug Enforcement Administration (DEA). Category 1 controlled substances currently have no recognized medical use in the United States, lack a recognized safety profile for use under medical supervision, and have a high potential for abuse. It is a hallucinogen.

These protocols are for reference only. InvivoChem does not independently validate these methods.

Physicochemical Properties

Molecular Formula	C10H13NO3
Molecular Weight	195.21512
Exact Mass	195.089
CAS #	74698-47-8
PubChem CID	98528
Appearance	Typically exists as solid at room temperature
LogP	1.7
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	3
Heavy Atom Count	14
Complexity	188
Defined Atom Stereocenter Count	0
InChi Key	FNDCTJYFKOQGTL-UHFFFAOYSA-N
InChi Code	InChI=1S/C10H13NO3/c1-7(11-12)4-8-2-3-9-10(5-8)14-6-13-9/h2-3,5,7,11-12H,4,6H2,1H3
Chemical Name	N-[1-(1,3-benzodioxol-5-yl)propan-2-yl]hydroxylamine
Synonyms	N-OH-Mda; N-Hydroxy MDA; N-Hydroxy-3,4-methylenedioxyamphetamine
HS Tariff Code	2934.99.9001
Storage	Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Solubility Data

Solubility (In Vitro)	May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
Solubility (In Vivo)	Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2:* DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5:* 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.)

Solubility (In Vitro)

May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples

Solubility (In Vivo)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)

Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).

View More

Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)

Oral Formulations

Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).

View More

Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders

Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

(Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	5.1224 mL	25.6121 mL	51.2243 mL
	5 mM	1.0245 mL	5.1224 mL	10.2449 mL
	10 mM	0.5122 mL	2.5612 mL	5.1224 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

N-Hydroxy-3,4-methylenedioxyamphetamine
Base Information
- Chemical Name:N-Hydroxy-3,4-methylenedioxyamphetamine
- CAS No.:74698-47-8
- Molecular Formula:C10H13 N O3
- Molecular Weight:195.218
- Hs Code.:2932999099
- European Community (EC) Number:634-555-0
- UNII:SJE1T2B1A7
- DSSTox Substance ID:DTXSID30860972
- Nikkaji Number:J413.581D
- Wikipedia:3,4-Methylenedioxy-N-hydroxyamphetamine
- Wikidata:Q4043402
- ChEMBL ID:CHEMBL127313
- Mol file:74698-47-8.mol
Synonyms:N-hydroxy MDA;N-hydroxy methylenedioxyamphetamine;N-hydroxy-1-(3,4-methylenedioxyphenyl)-2-aminopropane;N-hydroxy-1-(3,4-methylenedioxyphenyl)-2-aminopropane hydrochloride;N-hydroxy-1-(3,4-methylenedioxyphenyl)-2-aminopropane, (+-)-isomer;N-hydroxy-3,4-methylenedioxyamphetamine;N-OH-MDA

This product is a nationally controlled contraband, and the Lookchem platform doesn’t provide relevant sales information.
Chemical Property of N-Hydroxy-3,4-methylenedioxyamphetamine

Chemical Property:
- Vapor Pressure:1.73E-05mmHg at 25°C
- Boiling Point:349.7°C at 760 mmHg
- PKA:13.76±0.50(Predicted)
- Flash Point:165.3°C
- PSA：50.72000
- Density:1.246g/cm³
- LogP:1.71600
- XLogP3:1.7
- Hydrogen Bond Donor Count:2
- Hydrogen Bond Acceptor Count:4
- Rotatable Bond Count:3
- Exact Mass:195.08954328
- Heavy Atom Count:14
- Complexity:188
Purity/Quality:
Safty Information:
- Pictogram(s):
- Hazard Codes:
MSDS Files:

SDS file from LookChem

Useful:
- Canonical SMILES:CC(CC1=CC2=C(C=C1)OCO2)NO
- UsesA structural analog of 3,4-Methylenedioxy Methamphetamine (M303985) aka “ecstasy”. Hallucinogen; CNS stimulant. Controlled substance.
Technology Process of N-Hydroxy-3,4-methylenedioxyamphetamine

There total 3 articles about N-Hydroxy-3,4-methylenedioxyamphetamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 31.0%

4676-39-5 1-(1,3-benzodioxol-5-yl)-2-propanone

74698-47-8 N-hydroxy-3,4-methylenedioxyamphetamine

Guidance literature:

With hydroxylamine; sodium cyanoborohydride;

Reference yield:

4764-17-4 3,4-methylenedioxyamphetamine

4676-39-5 1-(1,3-benzodioxol-5-yl)-2-propanone

555-64-6,14513-20-3 α-methyldopamine

74698-47-8

N-hydroxy MDA Product Information

N-hydroxy MDA is listed under Other and is intended for analytical research, quality control and pharmaceutical reference standard applications. The product is supplied by Clearsynth under CAT No. CS-TB-66235.

Clearsynth provides this compound for research and analytical use, with product information including CAS number, molecular formula, molecular weight and product enquiry details.

Technical Data

Product Name

N-hydroxy MDA

CAS No.

74698-47-8

CAT No.

CS-TB-66235

HSN Code

38229010

Country of Origin

Can be shipped from India, Canada and USA

Molecular Formula

–

Molecular Weight

195.22

Category

Other

Storage Condition

Refer MSDS for complete information.

Hazard Compound

Refer MSDS for complete information.

Description

Regulatory Description

N-hydroxy MDA is supplied with detailed characterization data compliant with regulatory guideline. N-hydroxy MDA can be used for analytical method development, method validation (AMV), Quality Control (QC), ANDA-related analytical work, and commercial pharmaceutical research applications.

Overview

Useful research chemical for a range of applications.

Synonyms

N-hydroxy MDA

Application Notes

Useful research chemical for a range of applications.

References

CAS
PubChem
Wikipedia

N-hydroxy-3,4-methylenedioxyamphetamine

Guidance literature:

With rabbit liver cytochrome P₄₅₀IIB₄; 1,2-dilauroylphosphatidylcholine; NADPH; NADPH-cytochrome P₄₅₀ reductase; ascorbic acid; In water; at 37 ℃; for 0.0833333h; Mechanism; other (methylenedioxy)phenyl compounds; also in the hydroxyl radical system (ferric chloride, EDTA, potassium phosphate buffer, pH 7.4); demethylenation reaction;

DOI:10.1021/jm00113a028

N-Hydroxy-3,4-methylenedioxyamphetamine

Base Information

Chemical Name:N-Hydroxy-3,4-methylenedioxyamphetamine
CAS No.:74698-47-8
Molecular Formula:C10H13 N O3
Molecular Weight:195.218
Hs Code.:2932999099
European Community (EC) Number:634-555-0
UNII:SJE1T2B1A7
DSSTox Substance ID:DTXSID30860972
Nikkaji Number:J413.581D
Wikipedia:3,4-Methylenedioxy-N-hydroxyamphetamine
Wikidata:Q4043402
ChEMBL ID:CHEMBL127313
Mol file:74698-47-8.mol

Synonyms:N-hydroxy MDA;N-hydroxy methylenedioxyamphetamine;N-hydroxy-1-(3,4-methylenedioxyphenyl)-2-aminopropane;N-hydroxy-1-(3,4-methylenedioxyphenyl)-2-aminopropane hydrochloride;N-hydroxy-1-(3,4-methylenedioxyphenyl)-2-aminopropane, (+-)-isomer;N-hydroxy-3,4-methylenedioxyamphetamine;N-OH-MDA

This product is a nationally controlled contraband, and the Lookchem platform doesn’t provide relevant sales information.

Chemical Property of N-Hydroxy-3,4-methylenedioxyamphetamine

Chemical Property:

Vapor Pressure:1.73E-05mmHg at 25°C
Boiling Point:349.7°C at 760 mmHg
PKA:13.76±0.50(Predicted)
Flash Point:165.3°C
PSA：50.72000
Density:1.246g/cm³
LogP:1.71600
XLogP3:1.7
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:195.08954328
Heavy Atom Count:14
Complexity:188

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:CC(CC1=CC2=C(C=C1)OCO2)NO
UsesA structural analog of 3,4-Methylenedioxy Methamphetamine (M303985) aka “ecstasy”. Hallucinogen; CNS stimulant. Controlled substance.

Technology Process of N-Hydroxy-3,4-methylenedioxyamphetamine

There total 3 articles about N-Hydroxy-3,4-methylenedioxyamphetamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 31.0%

: 4676-39-5 1-(1,3-benzodioxol-5-yl)-2-propanone

: 74698-47-8 N-hydroxy-3,4-methylenedioxyamphetamine

Guidance literature:: With hydroxylamine; sodium cyanoborohydride;

Reference yield:

: 4764-17-4 3,4-methylenedioxyamphetamine

: 4676-39-5 1-(1,3-benzodioxol-5-yl)-2-propanone

: 555-64-6,14513-20-3 α-methyldopamine

: 74698-47-8 N-hydroxy-3,4-methylenedioxyamphetamine

Guidance literature:: With rabbit liver cytochrome P₄₅₀IIB₄; 1,2-dilauroylphosphatidylcholine; NADPH; NADPH-cytochrome P₄₅₀ reductase; ascorbic acid; In water; at 37 ℃; for 0.0833333h; Mechanism; other (methylenedioxy)phenyl compounds; also in the hydroxyl radical system (ferric chloride, EDTA, potassium phosphate buffer, pH 7.4); demethylenation reaction;

DOI:10.1021/jm00113a028

N-hydroxy MDA | CS-TB-66235 | CAS 74698-47-8 | Clearsynth

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N-Hydroxy-3,4-methylenedioxyamphetamine is a novel and potent bioactive compound

CAS: 74698-47-8 – 1- (1,3-benzodioxol-5-yl)-N-hydroxypropan…

74698-47-8: (±)-N-Hydroxy-3,4- (methylenedioxy)amphetamine, 1,3-Benzodioxole-5-ethanamine, N-hydroxy-α-methyl-, 1,3 …
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3,4-Methylenedioxy-N-hydroxyamphetamine (MDOH, MDH), also known as N-hydroxy-MDA, is an entactogen, psychedelic, and …
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3,4-Methylenedioxy-N-hydroxyamphetamine (MDOH, MDH), also known as N-hydroxy-MDA, is an entactogen, psychedelic, and …
N-hydroxy-1- (3,4-methylenedioxyphenyl)-2-aminopropane

May 4, 2023 · N-hydroxy-1- (3,4-methylenedioxyphenyl)-2-aminopropane (CAS 74698-47-8) information, including chemical …
74698-47-8 – ChemBK

Name:N-hydroxy-1- (3,4-methylenedioxyphenyl)-2-aminopropane,CAS:74698-47-8.Molecular Fomula:C10H13NO3,Molar …
3,4-Methylenedioxy-N-hydroxyaMphetaMine – ChemBK

Name:N-hydroxy-1- (3,4-methylenedioxyphenyl)-2-aminopropane,CAS:74698-47-8.Molecular Fomula:C10H13NO3,Molar …

3,4-Methylenedioxy-N-hydroxyaMphetaMine – Names and Identifiers

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United States

MDOH is a schedule I controlled substance in the United States.^[4]

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N-Hydroxy-3,4-methylenedioxyamphetamine

N-hydroxy MDA Product Information

Technical Data

Description

N-Hydroxy-3,4-methylenedioxyamphetamine

3,4-Methylenedioxy-N-hydroxyaMphetaMine – Names and Identifiers

Legal status

Canada

United States

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