Alkaloids

Nicotine Synthesis

Medicinal Uses

1. Nicotine ka therapeutic use limited hota hai – lekin research dikhati hai ki yeh Parkinson’s disease, Alzheimer’s disease, depression aur anxiety ke treatment me kaam aa sakta hai.

2. Nicotine salts – yeh mainly insecticides banane me use hote hain.

3. Hygrine (C₈H₁₅NO) –

Ye ek pyrrolidine alcohol hota hai, jo zyada tar coca leaves me milta hai.

Properties:

• Thick yellow oil jaisa hota hai.

• Taste aur odour pungent (tez) hota hai.

• Boiling point range: 193 to 195°C

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Structure Elucidation

1. Molecular formula: C₈H₁₅NO–

Is formula se pata chalta hai ki molecule me keto group hai aur tertiary nitrogen atom present hai.

Jab isse formic acid ke sath oxidise karte hain, toh Hygrinic acid banta hai.

Reaction:

C₈H₁₅NO \xrightarrow[\text{oxidation (O₂)}]{} C₆H₁₁NO₂

2. Hygrinic acid ko dry distillation karne par N-methyl pyrrolidine milta hai — isse confirm hota hai ki hygrinic acid me pyrrolidine ring present hai.

Reaction Diagram

Yahan tumhare notes me (+)-Hygrinic acid ka decarboxylation reaction dikhaya gaya hai:

Jab Hygrinic acid ko heat dete hain, toh yeh N-methyl pyrrolidine + CO₂ banata hai.

Iska matlab carboxylic acid group ring ke position-2 par hai, kyunki decarboxylation easily ho raha hai.

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Point (3) – Presence of N–CH₃ group

N–CH₃ group ka presence confirm hota hai Herzemeier determination se.

Is test me compound ko HI ke saath heat karke CH₃I (methyl iodide) banate hain aur measure karte hain.

Point (4) – Formation of Hygrinic acid on oxidation of Hygrine

1. Jab Hygrine ka oxidation hota hai, toh Hygrinic acid banta hai.

2. Is reaction se yeh pata chalta hai ki Hygrine ke C₂ position par (N-methyl pyrrolidine ring ke doosre carbon par) ek side chain present hai.

3. Ye side chain ka molecular fragment C₃H₅O hota hai.

• C₃ → teen carbon atoms

• H₅ → paanch hydrogen atoms

• O → ek oxygen atom

4. Jab is side chain ka oxidation hota hai, toh sirf ek carbon-containing carboxylic acid milta hai → iska matlab side chain me baaki carbon atoms kisi aur functional group me hote hain.

5. Yeh functional group keto group (C=O) hota hai.

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💡 Conclusion:

Side chain ka structure aisa hona chahiye jo:

• C₃H₅O formula match kare,

• C₂ position pe attached ho,

• Aur oxidation se ek-carbon ka carboxylic acid banaye.

Isi basis par Hygrine ke 2 possible structures (A & B) propose kiye gaye.

Top Reaction (Oxidation Step)

Page ke top me tumhare notes dikhate hain ki Hygrine ke C₂ position par jo C₃H₅O side chain hoti hai, uska oxidation hone par ek carbon-containing carboxylic acid milta hai.

Do possible structures propose kiye gaye hain:

Structure A: N-methyl pyrrolidine ring ke C₂ pe CH₂–C(=O)–CH₃ (acetonyl group) attached hai.

Structure B: Side chain thoda alag arrangement me attached hai.

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Point (5) – Structure Confirmation

Structure (A) me ek acetonyl group (CH₃–CO–CH₂–) hota hai.

Iska proof hai ki yeh Iodoform test positive deta hai.

Reason: Iodoform test ketone group ke liye hota hai, specifically methyl ketone (C=O–CH₃).

Agar methyl ketone hota hai, to yellow precipitate (CHI₃) banta hai.

Isliye confirm hota hai ki structure me C=O–CH₃ group present hai.

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Synthesis of Hygrine (Structure A Confirmation ka dusra proof)

Hygrine ko banane ke liye γ-N-methylaminobutyraldehyde ko ethyl acetoacetate ke saath condense karte hain (pH ≈ 7).

Reaction ka result: N-methyl pyrrolidine ring ban jata hai jisme C₂ pe acetonyl group hota hai → jo exactly Structure A ka form hai.

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💡 Key Points:

1. Oxidation data + Iodoform test dono confirm karte hain ki Hygrine me methyl ketone present hai.

2. Laboratory synthesis bhi same structure

banata hai → isliye Structure A sahi hota hai.

Synthesis of Hygrinic acid by Willstater method

🔹 Starting Material

Hum use karte hain Na salt of malonic acid (diethyl malonate ka sodium salt).

Reagents:

• 1. Br–(CH₂)₃–Br (1,3-dibromopropane)

• 2. Br₂

• 3. CH₃–NH₂ (Methylamine)

• 4. Hydrolysis + Decarboxylation

🔹 Step 1: Alkylation

Sodium salt of malonic ester (–CH⁻ from malonic ester) nucleophile banega.

Ye 1,3-dibromopropane par attack karega.

Result: ek lamba chain banega jisme malonic ester attach hoga aur Br side mai nikal jayega.

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🔹 Step 2: Bromination (Br₂ treatment)

Chain mai double bond ke paas ya reactive carbon par Br₂ add hota hai.

Isse ek dibromo compound banta hai.

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🔹 Step 3: Reaction with Methylamine (CH₃–NH₂)

Ab methylamine (nucleophile) Br ko replace karega.

Yaha se ek N–CH₃ group introduce hota hai (–NHCH₃).

Side reaction mai HBr nikalta hai.

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🔹 Step 4: Cyclization (Ring Closure)

Chain apne aap band hokar pyrrolidine type ring banata hai (5-membered nitrogen containing ring).

Yehi sabse important step hai kyunki yahi se Hygrinic acid ka skeleton ready hota hai.

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🔹 Step 5: Hydrolysis + Decarboxylation

Ester groups (–COOEt) ko hydrolyze karte hain → –COOH.

Fir heating par ek –COOH group decarboxylate ho jata hai.

Final Product = Hygrinic Acid (pyridine ring ke saath –CH₃ aur –COOH groups).

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🔹 Overall Samajh Lo

1. Malonic ester → alkylation with 1,3-dibromopropane.

2. Bromination → dibromo derivative.

3. CH₃–NH₂ attack → nitrogen introduce.

4.

Cyclization → 5-membered heterocycle.

5. Hydrolysis + Decarboxylation → Hygrinic acid. ✅

Medical use hygrine

Hygrine ka use hota hai:

Sedative (calming effect)

Hypnotic (sleep-inducing)

Laxative (constipation relief)

Diuretic (urine output increase karne wala)

Terpene kya hai ?

Terpenes highly fragrant organic compounds hote hain jo plants aur herbs ko unki characteristic smell/odor dete hain.

Matalab smjho

Terpenes – Simple Definition

Terpenes ek type ke organic compounds hote hain (yaani carbon-based molecules).

Ye mostly plants me paaye jaate hain.

Inka special feature ye hai ki ye plants ko khushboo/smell dete hain.

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Example se samjho

Orange ki smell 🍊 → terpenes.

Eucalyptus oil ki fragrance 🌿 → terpenes.

Rose aur Jasmine ki khushboo 🌹🌸 → terpenes.

Pine tree (devdar) ka woody smell 🌲 → terpenes.

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Why “highly fragrant”?

Kyuki terpenes me aise structures hote hain jo easily evaporate (volatile) hote hain aur hamari nose ke receptors ko stimulate karke smell produce karte hain.

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👉 Matlab ek line me:

“Terpenes wo natural compounds hain jo plants me paaye jaate hain aur unki khushboo (fragrance) ka asli source hote hain.”

Definition:

Terpenes highly fragrant organic compounds hote hain jo plants aur herbs ko unki characteristic smell/odor dete hain.

Example: Flowers (rose, jasmine), Fruits (lemon, orange), Leaves (mint, eucalyptus), Wood (sandalwood).

Structure:

Naturally occurring organic compounds.

Carbon + Hydrogen + Oxygen se bante hain.

Aromatic nature ke nahi hote, lekin alag-alag structures me arrange hote hain.

Inhe isoprene units (2-methyl-1,3-butadiene) me todha jaa sakta hai.

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Isoprene & Isoprene Rule

Isoprene Unit:

CH₂=C(CH₃)–CH=CH₂

Isoprene Rule (Wallach Rule):

Terpenoids ke skeleton hamesha 2 ya usse zyada isoprene units se bane hote hain.

Is wajah se terpenoids ko isoprenoids bhi kaha jata hai.

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Special Isoprene Rule

Terpenoids me isoprene units link hote hain C₁–C₄ positions ke through.

Is type ki linkage ko head-to-tail union kehte hain.

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✅ Summary ek line me:

Terpenes = natural fragrance compounds made of isoprene units (C₅ rule) → Isoprene units join "head

-to-tail" to give different classes of terpenoids.